Water → tert-Butyl ((1S,2R)-1-benzyl-2-hydroxy-3-(isobutyl((4-nitrophenyl)sulfonyl)amino)propyl)carbamate

HRID 658522Notes

Reaction equation

HRID 658522 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:32]([C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)([O-:34])=[O:33].O>C(O)(C)C>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C@H:9]([OH:16])[CH2:10][N:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[S:41]([C:38]1[CH:37]=[CH:36][C:35]([N+:32]([O-:34])=[O:33])=[CH:40][CH:39]=1)(=[O:42])=[O:43])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9902339tert-Butyl ((2S,3R)-3-hydroxy-4-((2-methylpropyl)amino)-1-phenylbutan-2-yl)carbamate

Product 1

HCID 10279676tert-Butyl ((1S,2R)-1-benzyl-2-hydroxy-3-(isobutyl((4-nitrophenyl)sulfonyl)amino)propyl)carbamateYield 96.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
62.5 °C

Procedure

7.5 g (22.3 mmol) of (1S,2R)-(1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid tert-butyl ester and 2.7 g (26.8 mmol, 1.2 equiv) of triethylamine are dissolved in 100 g of isopropanol and heated to 60-65° C. 5.41 g (24.5 mmol, 1.1 eq) p-nitrophenyl-sulfonyl chloride are added in several portions within 30 minutes. The reaction mixture is kept at 60° C. for another 30 minutes. 10 g of water are added and the suspension is stirred for an additional 30 minutes at 60° C. The mixture is cooled to 25° C. within 90 min and the product is filtered off, washed with a mixture of isopropanol/water (1:1 v/v) and dried under vacuum to yield 11.23 g (96.5%) of white (1S,2R)-{1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester.

Workup

  1. temperatureThe mixture is cooled to 25° C. within 90 min
  2. filtrationthe product is filtered off
  3. washwashed with a mixture of isopropanol/water (1:1 v/v)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b49c6ee5fc4d41929ace26a6e687e36f
Source dataset
uspto-grants-2011_12
Patent number
US08076513B2

Reaction notes

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