Tetrahydrofuran → tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-nitrophenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

HRID 29191

Reaction equation

HRID 29191 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:9]([OH:18])[CH2:10][NH:11]OC1CCCC1)([CH3:4])([CH3:3])[CH3:2].[N+:27]([C:30]1[CH:31]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28].[CH2:40]1[CH2:44][O:43][CH2:42][CH2:41]1.[CH:45](N(C(C)C)CC)(C)C>CCOC(C)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@@H:9]([OH:18])[CH:10]([NH:11][S:36]([C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=1)(=[O:38])=[O:37])[O:43][CH:44]1[CH2:40][CH2:41][CH2:42][CH2:45]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 84763-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21356391tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate

Product 1

HCID 86585039tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-nitrophenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate (0.52 g, 1.4 mmol) was combined with 3-nitrobenzenesulfonyl chloride (0.47 g, 2.1 mmol) in freshly distilled THF (5 ml). Diisopropylethylamine (0.74 ml, 4.3 mmol) was added and the reaction was stirred at room temperature overnight. Reaction mixture was diluted in EtOAc and washed with 0.5 N KHSO4, and brine. Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purication by flash chromatography (1:4/EtOAc/Hex gradient to 1:3, to 1:2, to 1:1 and then to 2:1). Recovered 0.44 g (56%) of the product as a white foam. Rf=0.45 (2:1 EtOAc/Hex), 1H NMR (CDCl3) 8.67 (1H, s), 8.49 (1H, d), 8.08 (1H, d), 7.77 (1H, t), 7.36-7.17 (5H, m), 4.88 (1H,m), 4.62 (1H,b), 3.88-3.71 (2H,m), 3.41 (1H,b), 3.07 (1H,b), 2.98-2.79 (3H,m), 1.92-1.75 (4H,m), 1.73-1.52 (4H,m), 1.45 (9H,s).

Workup

  1. customReaction mixture
  2. washwashed with 0.5 N KHSO4, and brine
  3. dry with materialOrganic phase was dried with MgSO4 and solvent
  4. customwas removed in vacuo
  5. customRecovered 0.44 g (56%) of the product as a white foam

Sources & evidence

ORD record
ord-3eba50de559c4b22b5d625c8be8ad67c
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Linked notes

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