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57653-35-7

57653-35-7 Structure

57653-35-7 Structure
IdentificationBack Directory
[Name]

CIS-ZHPROME
[CAS]

57653-35-7
[Synonyms]

CIS-ZHPROME
CIS-ZHPROME USP/EP/BP
N-CBZ-CIS-4-HYDROXY-L-PROLINE METHYL ESTER
(4S)-1-Cbz-4-hydroxy-L-proline methyl ester
N-CARBOBENZYLOXY-(4S)-HYDROXY-L-PROLINE METHYL ESTER
Methyl (2S,4S)-1-Cbz-4-Hydroxypyrrolidine-2-carboxylate
(2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
O1-Benzyl O2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
1-O-benzyl 2-O-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
(2S,4S)-1-(Benzyloxycarbonyl)-2-(methoxycarbonyl)-4-hydroxypyrrolidine
1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 2-methyl 1-(phenylmethyl) ester, (2S,4S)-
[Molecular Formula]

C14H17NO5
[MDL Number]

MFCD09954934
[MOL File]

57653-35-7.mol
[Molecular Weight]

279.29
Chemical PropertiesBack Directory
[Melting point ]

80-85°C
[Boiling point ]

422.8±45.0 °C(Predicted)
[density ]

1.313±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[form ]

solid
[pka]

14.25±0.40(Predicted)
[Appearance]

White to off-white Solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H319
[Precautionary statements ]

P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

36
[Safety Statements ]

26
[WGK Germany ]

2
Spectrum DetailBack Directory
[Spectrum Detail]

CIS-ZHPROME(57653-35-7)1HNMR
Hazard InformationBack Directory
[Synthesis]

1,2-Pyrrolidinedicarboxylic acid, 4-(benzoyloxy)-, 2-methyl 1-(phenylmethyl) ester, (2S,4S)-

1527519-52-3

CIS-ZHPROME

57653-35-7

Potassium carbonate (9.1 g, 65.8 mmol) was added to a solution of compound D (23 g, 65.8 mmol) in methanol (100 mL) at 0 °C and the reaction mixture was stirred at room temperature for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the mixture was filtered. The filtrate was concentrated under vacuum to remove methanol, and the residue was dissolved in ethyl acetate, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 4/1 to 1/1 gradient elution) to afford the target product (2S,4S)-N-CBZ-4-hydroxyproline methyl ester (12.6 g, 70% yield) as a light yellow oil.

[References]

[1] Patent: WO2014/32, 2014, A1. Location in patent: Page/Page column 59
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