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

HRID 1166497Notes

Reaction equation

HRID 1166497 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-8f6907304d6543119c0e82566b7d8bcf
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Reaction notes

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