Z-Hyp(Tbu)-OH → (2S,4S)-4-amino-2-(5-phenyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1477535

Reaction equation

HRID 1477535 reaction equation
C(OC(N1C[C@H](OC(C)(C)C)C[C@H]1C(O)=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24]([O:31][C:32]([N:34]1[CH2:38][C@@H:37]([NH2:39])[CH2:36][C@H:35]1[C:40]1[O:41][CH:42]=[CH:43][N:44]=1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([O:31][C:32]([N:34]1[CH2:38][C@@H:37]([NH2:39])[CH2:36][C@H:35]1[C:40]1[O:41][C:42]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:43][N:44]=1)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 6950951Z-Hyp(Tbu)-OHHCID 89768242(2S,4S)-4-Amino-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 89768393(2S,4S)-4-amino-2-(5-phenyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Procedure

(2S,4S)-4-amino-2-(5-phenyl-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester was prepared from (2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester in a similar reaction sequence used in the preparation of (2S,4S)-4-amino-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester. MS calcd. for C21H22N3O3 [(M+H)+] 364, obsd. 364.

Sources & evidence

ORD record
ord-ee40495a29e64e9fa21b624d0868538e
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Linked notes

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