4-Nitrobenzenesulfonyl chloride → 3-(4-Benzyloxy-phenyl)-2-[4-methyl-2-(4-nitro-benzenesulfonylamino)-pentanoylamino]-propionic acid tert-butyl ester

HRID 2230319Notes

Reaction equation

HRID 2230319 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH:7]([NH:23][C:24](=[O:31])[CH:25]([NH2:30])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N+:33]([C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1)([O-:35])=[O:34].C(N(CC)C(C)C)(C)C>CN(C1C=CN=CC=1)C.C1C=CC=CC=1.C(OC)(C)(C)C>[C:1]([O:5][C:6](=[O:32])[CH:7]([NH:23][C:24](=[O:31])[CH:25]([NH:30][S:42]([C:39]1[CH:38]=[CH:37][C:36]([N+:33]([O-:35])=[O:34])=[CH:41][CH:40]=1)(=[O:43])=[O:44])[CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 540817292-(2-Amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 700591343-(4-Benzyloxy-phenyl)-2-[4-methyl-2-(4-nitro-benzenesulfonylamino)-pentanoylamino]-propionic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of the product from Example AI ([S-(R*,R*)]-2-(2-amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (308 mg, 0.70 mmol), 4-nitrobenzenesulfonyl chloride (190 mg, 0.77 mmol), N,N-diisopropylethyl-amine (181 mg, 1.4 mmol) and DMAP (20 mg), in benzene (5 mL) was heated under reflux for 3 hours, then concentrated in vacuo and the residue dissolved in ethyl acetate, and washed with saturated NaHCO3 solution, water, and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The tan solid thus obtained was triurated in warm tert-butylmethyl ether, and filtered to give 419 mg (95%) of the title compound as a white solid, mp=121-123° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 solution, water, and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe tan solid thus obtained
  8. filtrationfiltered

Sources & evidence

ORD record
ord-8b8c24e72b38407abd457f23b161690b
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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