4-Nitrobenzenesulfonyl chloride → HCID 131733459, compound

HRID 2278368Notes

Reaction equation

HRID 2278368 reaction equation
[NH2:1][C@@H:2]([C:12]1[S:16][C:15]([CH2:17][NH:18][C:19](=[O:39])[C@H:20]([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:14][CH:13]=1)[CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].C(N(C(C)C)CC)(C)C.[N+:49]([C:52]1[CH:57]=[CH:56][C:55]([S:58](Cl)(=[O:60])=[O:59])=[CH:54][CH:53]=1)([O-:51])=[O:50]>ClCCl>[Si:5]([O:4][CH2:3][C@H:2]([C:12]1[S:16][C:15]([CH2:17][NH:18][C:19](=[O:39])[C@H:20]([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:14][CH:13]=1)[NH:1][S:58]([C:55]1[CH:54]=[CH:53][C:52]([N+:49]([O-:51])=[O:50])=[CH:57][CH:56]=1)(=[O:59])=[O:60])([C:8]([CH3:9])([CH3:10])[CH3:11])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 131733457HCID 131733457, compound

Product 1

HCID 131733459HCID 131733459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-({5-[(1R)-1-amino-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-thiophen-2-yl}methyl)-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (125 mg, 0.220 mmol) in dichloromethane (4.4 mL) was treated with diisopropylethylamine (0.046 mL, 0.264 mmol) and solid p-nitrobenzensulfonyl chloride (59 mg, 0.264 mmol) and the mixture was stirred at room temperature for 18 hours, quenched with saturated NaHCO3 (0.5 mL), diluted with DCM, washed with sat. NaHCO3, dried over MgSO4, filtered and concentrated. The crude was purified on silica gel 10%-50% ethyl acetate in hexane to provide the title compound. 1H NMR (CD3)2CO) δ 8.39 (2H), 8.05 (2H), 7.67 (1H), 7.41 (5H), 7.30-7.15 (6H), 6.65 (1H), 6.42 (1H), 6.30 (1H), 5.10 (1H), 4.72 (1H), 4.50 (1H), 4.23 (1H), 4.13 (1H), 3.82 (2H), 3.49 (3H), 0.84 (9H), 0.01 (6H).

Workup

  1. customquenched with saturated NaHCO3 (0.5 mL)
  2. additiondiluted with DCM
  3. washwashed with sat. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified on silica gel 10%-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8390d35b64bf4f289887deab6585ad67
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

Loading…