Trifluoroacetic acid → HCID 131715833, compound

HRID 2292330Notes

Reaction equation

HRID 2292330 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][C:41]=1[OH:42])[C:5]([NH:7][N:8]1[CH2:12][CH2:11][N:10]([C:13]([NH:15][S:16]([NH:19][C:20]([N:22]2[CH2:25][C@H:24]([NH:26]C(=O)OCC3C=CC=CC=3)[C:23]2=[O:37])=[O:21])(=[O:18])=[O:17])=[O:14])[C:9]1=[O:38])=[O:6].[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].C1(SC)C=CC=CC=1>>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[NH2:26][C@H:24]1[CH2:25][N:22]([C:20]([NH:19][S:16]([NH:15][C:13]([N:10]2[CH2:11][CH2:12][N:8]([NH:7][C:5](=[O:6])[C:4]3[CH:39]=[CH:40][C:41]([OH:42])=[C:2]([OH:1])[CH:3]=3)[C:9]2=[O:38])=[O:14])(=[O:18])=[O:17])=[O:21])[C:23]1=[O:37]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 86742702HCID 86742702, compound

Product 1

HCID 131715833HCID 131715833, compound

Procedure

(S)-[1-[[[[[[3-[(3,4-Dihydroxybenzoyl)amino]-2-oxo-1-imidazolidinyl]carbonyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (1.4 g) was added to a mixture of 6 ml of trifluoroacetic acid and 1.5 ml of thioanisole. The mixture was stirred overnight at room temperature. The trifluoroacetic acid was removed in vacuo and the residue triturated with ether to yield 1.4 g of crude (S)-N-[[[(3-amino-2-oxo-1-azetidinyl)carbonyl]amino]sulfonyl]-3-[(3,4-dihydroxybenzoyl)amino]-2-oxo-1-imidazolidinecarboxamide, trifluoroacetate salt.

Workup

  1. customThe trifluoroacetic acid was removed in vacuo
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-e9c74aa294e949dcb1a2e31b35ca625a
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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