Proline benzyl ester hydrochloride → 1-[(R)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester

HRID 716529Notes

Reaction equation

HRID 716529 reaction equation
COC(N[C@H](C1C=CC=CC=1)C(O)=O)=O.Cl.C(OC(=O)[C@@H]1CCCN1)C1C=CC=CC=1.[CH2:32]([O:39][C:40]([C@@H:42]1[CH2:46][CH2:45][CH2:44][N:43]1[C:47](=[O:63])[C@H:48]([NH:55][C:56]([O:58][C:59](C)(C)C)=[O:57])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:32]([O:39][C:40]([C@@H:42]1[CH2:46][CH2:45][CH2:44][N:43]1[C:47](=[O:63])[C@H:48]([NH:55][C:56]([O:58][CH3:59])=[O:57])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 2733413Proline benzyl ester hydrochlorideHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 15288611(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Product 1

HCID 542807701-[(R)-methoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid benzyl ester

Procedure

Compound 32 was synthesized from compound 31 and L-proline benzyl ester hydrochloride, following the procedure as described for compound 2a, as a white crystallized solid. MS (ESI, EI+) m/z=397 (MH+).

Workup

  1. customas a white crystallized solid

Sources & evidence

ORD record
ord-bdbc014805974eecb0682ee5456b2aad
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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