Acetyl chloride → (S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

HRID 1814366Notes

Reaction equation

HRID 1814366 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:19])=[O:18])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C(N1CC[O:41][CH2:40][CH2:39]1)C.C(Cl)(=O)C>ClCCl>[C:1]([O:5][C:6](=[O:35])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:40](=[O:41])[CH3:39])=[CH:22][C:21]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:19])=[O:18])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 7525EthylmorpholineHCID 69692490(S)-3-(4-amino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

Product 1

HCID 69692085(S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl esterYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 11.2 g (21.7 mmol) (S)-3-(4-amino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester and 50 mL dichloromethane and cooled to 0° C. in an ice/water bath. 3.2 mL (25 mmol) N-ethylmorpholine was added, followed by dropwise addition of 1.71 mL (24 mmol) acetyl chloride. After 10 min reaction time, TLC analysis showed complete reaction. The mixture was transferred to a separatory funnel and washed with 50 mL water, 50 mL brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give 12 g (21.8 mmol, 100%) of (S)-3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester as a brown oil. MS (APCI) m/z 549.1 (M−1), 459.1 (M-CH2Ph).

Workup

  1. customAfter 10 min reaction time, TLC analysis
  2. customreaction
  3. customThe mixture was transferred to a separatory funnel
  4. washwashed with 50 mL water, 50 mL brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2849164e1cea419b90369af36ce9d4e9
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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