HCID 67520568, compound → HCID 68281374, compound

HRID 1923977Notes

Reaction equation

HRID 1923977 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:37][CH2:38][NH:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])[CH2:15][CH2:16][CH2:17][C@H:18]([N:22](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:19]([OH:21])=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[NH2:22][C@@H:18]([CH2:17][CH2:16][CH2:15][N:14]([CH2:37][CH2:38][NH:39][C:40]([O:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[O:41])[CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:19]([OH:21])=[O:20]

Participants

3

Reactant 1

HCID 67520568HCID 67520568, compound

Product 1

HCID 68281374HCID 68281374, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2S)-5-[bis(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]-2-{bis[(tert-butoxy)carbonyl]amino}pentanoic acid (1.82 g, 3.14 mmol) in TFA (20 mL) was stirred overnight. The TFA was removed under reduced pressure to give (2S)-2-amino-5-[bis(2-{[(benzyloxy)carbonyl]amino}ethyl)amino]pentanoic acid XXXII as a light brown foam (1.70 g, 2.83 mmol, 90% yield). ESIMS found for C25H34N4O6 m/z 487 (M+H).

Workup

  1. customThe TFA was removed under reduced pressure

Sources & evidence

ORD record
ord-28f49133b0214fcf8247ac1434b58999
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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