Benzyloxycarbonylglycine → HCID 24988508, compound

HRID 406505Notes

Reaction equation

HRID 406505 reaction equation
[CH3:1][CH:2]1[C@H:6]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:5][CH2:4][NH:3]1.[CH2:15]([O:22][C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:10]([O:9][C:8](=[O:14])[NH:7][C@@H:6]1[CH2:5][CH2:4][N:3]([C:27](=[O:28])[CH2:26][NH:25][C:23]([O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:24])[C@@H:2]1[CH3:1])([CH3:13])([CH3:12])[CH3:11].[C:10]([O:9][C:8](=[O:14])[NH:7][C@@H:6]1[CH2:5][CH2:4][N:3]([C:27](=[O:29])[CH2:26][NH:25][C:23]([O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:24])[C@H:2]1[CH3:1])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 14349BenzyloxycarbonylglycineHCID 86621724HCID 86621724, compound

Product 2

HCID 24988508HCID 24988508, compoundHCID 59764941HCID 59764941, compound

Procedure

[(2R,3R)-1-(2-Benzyloxycarbonylamino-acetyl)-2-methyl-pyrrolidin-3-yl]-carbamic acid tert-butyl ester and [(2S,3R)-1-(2-benzyloxycarbonylamino-acetyl)-2-methyl-pyrrolidin-3-yl]-carbamic acid tert-butyl ester were synthesized from tert-butyl (3R)-2-methylpyrrolidin-3-ylcarbamate and 2-(benzyloxycarbonylamino)acetic acid using general procedure G. RP-HPLC (Table 1, Method d) Rt 5.57 min. (trans) and 5.53 min. (cis); m/z: (M+H)+ 392.

Workup

  1. customRP-HPLC (Table 1, Method d) Rt 5.57 min. (trans) and 5.53 min. (cis)

Sources & evidence

ORD record
ord-a1255ab0cce242a2be37b2fef22080d1
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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