Triethylamine → 3-(4-Benzyloxy-phenyl)-2-(2-methanesulfonylamino-4-methyl-pentanoylamino)-propionic acid tert-butyl ester

HRID 2230316Notes

Reaction equation

HRID 2230316 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.[CH3:40][S:41](Cl)(=[O:43])=[O:42].C(OCC)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:32])[CH:7]([NH:23][C:24](=[O:31])[CH:25]([NH:30][S:41]([CH3:40])(=[O:43])=[O:42])[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

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 540817292-(2-Amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 777683233-(4-Benzyloxy-phenyl)-2-(2-methanesulfonylamino-4-methyl-pentanoylamino)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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) (0.25 g, 1.7 mmol) and triethylamine (0.5 mL) in CH2Cl2 (10 mL) was treated with methansulfonyl chloride (0.25 mL). The resulting solution was stirred overnight at room temperature. The reaction mixture was treated with ethyl acetate (100 mL) and washed sequentially with aqueous 1N HCl solution (3×20 mL), saturated aqueous NaHCO3 solution (3×20 mL), and brine (3×20 mL). The organic phase was dried (MgSO4), filtered, and concentrated. The residue was purified by chromatography (silica gel, 1:1 ethyl acetate/heptane) to give the title compound as a pale peach powder (0.15 g, 51%), mp=83-84° C.

Workup

  1. washwashed sequentially with aqueous 1N HCl solution (3×20 mL), saturated aqueous NaHCO3 solution (3×20 mL), and brine (3×20 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (silica gel, 1:1 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-4bb87cb0d07d46acb9a98dfa4e627a25
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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