Trifluoroacetic acid → 2,6-Dimethyl-benzoic acid 3-({2-benzenesulfonyl-6-[(isoquinoline-1-carbonyl)-amino]-5-oxo-decahydro-2,4a-diaza-benzocyclooctene-4-carbonyl}-amino)-4-carboxy-2-oxo-butyl ester

HRID 722745Notes

Reaction equation

HRID 722745 reaction equation
[C:1]1([S:7]([N:10]2[CH2:35][CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([NH:22][C:23]([C:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=[CH:27][N:26]=4)=[O:24])[C:20](=[O:21])[N:13]3[CH:12]([C:36]([NH:38][CH:39]([CH2:54][C:55]([O:57]C(C)(C)C)=[O:56])[C:40](=[O:53])[CH2:41][O:42][C:43](=[O:52])[C:44]3[C:49]([CH3:50])=[CH:48][CH:47]=[CH:46][C:45]=3[CH3:51])=[O:37])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([S:7]([N:10]2[CH2:35][CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([NH:22][C:23]([C:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=[CH:27][N:26]=4)=[O:24])[C:20](=[O:21])[N:13]3[CH:12]([C:36]([NH:38][CH:39]([CH2:54][C:55]([OH:57])=[O:56])[C:40](=[O:53])[CH2:41][O:42][C:43](=[O:52])[C:44]3[C:45]([CH3:51])=[CH:46][CH:47]=[CH:48][C:49]=3[CH3:50])=[O:37])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69659652HCID 69659652, compound

Product 1

HCID 696600872,6-Dimethyl-benzoic acid 3-({2-benzenesulfonyl-6-[(isoquinoline-1-carbonyl)-amino]-5-oxo-decahydro-2,4a-diaza-benzocyclooctene-4-carbonyl}-amino)-4-carboxy-2-oxo-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 2,6-dimethyl-benzoic acid 3-({2-benzenesulfonyl-6-[(isoquinoline-1-carbonyl)-amino]-5-oxo-decahydro-2,4a-diaza-benzocyclooctene-4-carbonyl}-amino)-4-tert-butoxycarbonyl-2-oxo-butyl ester, 112, obtained above is treated with solution of trifluoroacetic acid (10 ml) and dichloromethane (10 ml). The mixture is stirred for 2 hours and solvent is removed in vacuo. The residue is purified by flash chromatography on silica gel (CH2Cl2/MeOH) to afford 120 mg of the desired product.

Workup

  1. customsolvent is removed in vacuo
  2. customThe residue is purified by flash chromatography on silica gel (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-e10daad105854692b230e1cec8a5e723
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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