Trifluoroacetic acid → N-(5-bromo-2-benzoxazolyl)-3-[[4-[3-oxo-3-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]propyl]benzoyl]amino]-L-alanine

HRID 1759718Notes

Reaction equation

HRID 1759718 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([NH:10][C@H:11]([C:33]([O:35]C(C)(C)C)=[O:34])[CH2:12][NH:13][C:14](=[O:32])[C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](=[O:31])[NH:24][C:25]4[NH:26][CH2:27][CH2:28][CH2:29][N:30]=4)=[CH:17][CH:16]=3)=[N:7][C:6]=2[CH:40]=1.C(O)(C(F)(F)F)=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([NH:10][C@H:11]([C:33]([OH:35])=[O:34])[CH2:12][NH:13][C:14](=[O:32])[C:15]3[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23](=[O:31])[NH:24][C:25]4[NH:26][CH2:27][CH2:28][CH2:29][N:30]=4)=[CH:19][CH:20]=3)=[N:7][C:6]=2[CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69733401(1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-[3-oxo-3-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]propyl]benzoyl]amino]-L-alaninate

Product 1

HCID 69709945N-(5-bromo-2-benzoxazolyl)-3-[[4-[3-oxo-3-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]propyl]benzoyl]amino]-L-alanineYield 117.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrolysis of the ester is carried out as in the previous examples, but starting from 56 mg of 10-7 and 2.5 ml of TFA in 2.5 ml of dichloromethane. 60 mg of 10-8 is obtained (in the form of the trifluoroacetic acid salt).

Sources & evidence

ORD record
ord-7e437443b5de48b5bfecf0b3ad336e46
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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