Acetyl chloride → (S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester

HRID 1814346Notes

Reaction equation

HRID 1814346 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:15])=[O:14])[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[C:39](Cl)(=[O:41])[CH3:40]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:39](=[O:41])[CH3:40])=[CH:18][C:17]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:14])=[O:15])[C:9]([NH2:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69692844(S)-3-(4-Amino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester

Product 1

HCID 69691767(S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(4-amino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester (1.41 g, 3.10 mmol) in methylene chloride (100 mL) and Et3N (0.44 mL, 3.10 mmol) was added acetyl chloride (0.25 mL, 3.1 mmol). The reaction was stirred for 3 h. The solvent was removed and replaced with EtOAc (150 mL). The organic solution was washed twice with 5% citric acid, saturated NaHCO3, water, and brine. The solution was dried over MgSO4, filtered, and the solvent was removed. The resulting crude product was purified using silica gel flash chromatography (20% hexanes in EtOAc). (S)-3-(4-Acetylamino-2-benzyloxy-benzenesulfonylamino)-succinamic acid tert-butyl ester was obtained in 63% yield (0.96 g) as an off white foam. MS (APCI) m/z 490.2 (M−1).

Workup

  1. customThe solvent was removed
  2. washThe organic solution was washed twice with 5% citric acid, saturated NaHCO3, water, and brine
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-8b11d8a10b81457781f2e9359f9ee6ba
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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