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Triethylamine → 3-(4-Benzyloxy-phenyl)-2(S)-[2(S)-(4-tert-butyl-benzenesulfonylamino)-4-methyl-pentanoylamino]-propionic acid tert-butyl ester

HRID 2230317
Notes
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Reaction equation

HRID 2230317 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].C(N(CC)CC)C.[C:40]([C:44]1[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=1)([CH3:43])([CH3:42])[CH3:41].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:32])[C@@H:7]([NH:23][C:24](=[O:31])[C@@H:25]([NH:30][S:50]([C:47]1[CH:48]=[CH:49][C:44]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:45][CH:46]=1)(=[O:52])=[O:51])[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 540817292-(2-Amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 700600743-(4-Benzyloxy-phenyl)-2(S)-[2(S)-(4-tert-butyl-benzenesulfonylamino)-4-methyl-pentanoylamino]-propionic acid tert-butyl ester
Yield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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) (0.20 g, 0.45 mmol) and triethylamine (0.13 mL, 0.90 mmol) in 5 mL of CHCl3 was cooled to 0° C. and treated with 4-tert-butylphenylsulfonyl chloride (0.10 g, 0.45 mmol). The reaction mixture was warmed to room temperature and treated with saturated aqueous NaHCO3. The organic phase was separated from the aqueous phase. The aqueous phase was extracted with additional CHCl3, and the combined organic extracts were dried MgSO4, filtered, and concentrated. The residue was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate). The chromatography product was crystallized from hot heptane/ethyl acetate to give the title compound as a white solid 0.20 g 70%), mp=142-143° C.

Workup

  1. customwas cooled to 0° C.
  2. customThe organic phase was separated from the aqueous phase
  3. extractionThe aqueous phase was extracted with additional CHCl3
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate)
  7. customThe chromatography product was crystallized from hot heptane/ethyl acetate

Sources & evidence

ORD record
ord-67168a69dbc34e30b7b758740b759fc5
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06423689B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes