Proline benzyl ester hydrochloride → (S,S)-1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester

HRID 716519Notes

Reaction equation

HRID 716519 reaction equation
CC(OC(N[C@H](C(O)=O)C1C=CC=CC=1)=O)(C)C.Cl.C(OC(=O)[C@@H]1CCCN1)C1C=CC=CC=1.[CH2:35]([O:42][C:43]([C@@H:45]1[CH2:49][CH2:48][CH2:47][N:46]1[C:50](=[O:66])[C@H:51]([NH:58][C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:42][C:43]([C@@H:45]1[CH2:49][CH2:48][CH2:47][N:46]1[C:50](=[O:66])[C@@H:51]([NH:58][C:59]([O:61][C:62]([CH3:64])([CH3:63])[CH3:65])=[O:60])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 2733413Proline benzyl ester hydrochlorideHCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 15288611(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Product 1

HCID 67239936(S,S)-1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Procedure

Compound 21 was synthesized from Boc-L-phenylglycine and L-proline benzyl ester hydrochloride, following the procedure as described for compound 2a, as a white crystallized solid. MS (ESI, EI+) m/z=439 (MH+).

Workup

  1. customas a white crystallized solid

Sources & evidence

ORD record
ord-197768ab70634cdfb5ca819a4d79a27f
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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