Triethylamine → HCID 54291668, compound

HRID 651335Notes

Reaction equation

HRID 651335 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:22])[C@H:11]([NH2:21])[CH2:12][C:13]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[O:30]([C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl>[CH2:2]([O:9][C:10](=[O:22])[C@H:11]([NH:21][S:43]([C:40]1[CH:39]=[CH:38][C:37]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:42][CH:41]=1)(=[O:45])=[O:44])[CH2:12][C:13]([N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)=[O:14])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27947564-Phenoxybenzene-1-sulfonyl chlorideHCID 69288519HCID 69288519, compound

Product 1

HCID 54291668HCID 54291668, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the title B compound, (2R)-amino-4-morpholin-4-yl-4-oxobutyric acid benzyl ester hydrochloride (420 mg, 1.28 mmol) in 5 mL of dichloromethane is treated with triethylamine (345 mg, 2.82 mmol) followed by a solution of 4-phenoxybenzenesulfonyl chloride (345 mg, 1.28 mmol) in 2 mL of dichloromethane. The reaction is stirred for 16 h, then partitioned between dichloromethane and water. The organic solution is washed with brine, dried over anhydrous MgSO4 and concentrated. Chomatography on silica gel (eluant; 3% MeOH in dichloromethane) affords 430 mg (64%) of (2R)-(4-phenyloxybenzenesulfonylamino)-4-morpholin-4-yl-4-oxobutyric acid benzyl ester as a white foam.

Workup

  1. custompartitioned between dichloromethane and water
  2. washThe organic solution is washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9002653767114ca19b2d89ab18507b9c
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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