Diisopropylethylamine → HCID 54527823, compound

HRID 1594532Notes

Reaction equation

HRID 1594532 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:28]([O:32][C:33](=[O:39])[C@@H:34]([CH:36]([CH3:38])[CH3:37])[NH2:35])([CH3:31])([CH3:30])[CH3:29]>ClCCl>[C:28]([O:32][C:33](=[O:39])[C@@H:34]([CH:36]([CH3:37])[CH3:38])[NH:35][S:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)(=[O:15])=[O:14])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6931638tert-butyl D-valinateHCID 122497414-(4-Bromophenoxy)benzene-1-sulfonyl chloride

Product 1

HCID 54527823HCID 54527823, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. suspension of 4-(4-bromophenoxy)benzene sulfonyl chloride (1.10 g, 3.16 mmol) in 20 mL of dichloromethane was added a solution of diisoproylethylamine (1.10 mL, 6.3 mmol) and D-valine tert-butyl ester (660 mg, 3.8 mol) in 11 mL of dichloromethane. The ice bath was removed, and the reaction was stirred for 3 h, diluted with 30 mL dichloromethane, and 30 ml of 1 M HCl was added. The layers were separated, and the aqueous layer was washed with 30 mL of dichloromethane. The combined dichloromethane fractions were washed with brine, dried over MgSO4, and concentrated. The residue was chromatographed on silica, eluting with 25% ethyl acetate in hexane, to give 980 mg (64%) of N-[4-(4-bromophenoxy)benzenesulfonyl]-D-valine t-butyl ester as a white foam.

Workup

  1. customThe ice bath was removed
  2. additiondiluted with 30 mL dichloromethane, and 30 ml of 1 M HCl
  3. additionwas added
  4. customThe layers were separated
  5. washthe aqueous layer was washed with 30 mL of dichloromethane
  6. washThe combined dichloromethane fractions were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica
  10. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-bcd4c57f18944b879ec91fe65f6af061
Source dataset
uspto-grants-2001_09
Patent number
USH0001992H1

Reaction notes

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