Benzoyl chloride → HCID 66769624, compound

HRID 1786650Notes

Reaction equation

HRID 1786650 reaction equation
[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:42])[NH:11][CH:12]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:13]([OH:34])[CH2:14][N:15]([S:20]([C:23]2[CH:24]=[CH:25][C:26]3[O:30][CH:29]=[C:28]([CH2:31][NH2:32])[C:27]=3[CH:33]=2)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.[C:43](Cl)(=[O:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(N(CC)CC)C>C1COCC1>[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:42])[NH:11][CH:12]([CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:13]([OH:34])[CH2:14][N:15]([S:20]([C:23]2[CH:24]=[CH:25][C:26]3[O:30][CH:29]=[C:28]([CH2:31][NH:32][C:43](=[O:50])[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:27]=3[CH:33]=2)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 66769815HCID 66769815, compound

Product 1

HCID 66769624HCID 66769624, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{3-[(3-Aminomethyl-benzofuran-5-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester from the previous step (20 mg, 33 umol) was dissolved in 0.5 mL THF. 5.8 uL (50 umol) benzoyl chloride and 7 uL (50 umol) triethylamine were added and the reaction was stirred at room temperature for 1 h. The reaction mixture was purified by prep TLC on the silica gel plate with ethyl acetate/hexanes=2/1 to afford 12 mg (17 umol, 52%) of product. MS 706 (MH+).

Workup

  1. customThe reaction mixture was purified by prep TLC on the silica gel plate with ethyl acetate/hexanes=2/1

Sources & evidence

ORD record
ord-0b020d2e3819488f85be6834a110dbfb
Source dataset
uspto-grants-2009_03
Patent number
US07507763B2

Reaction notes

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