Acetyl chloride → 3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic tert-butyl ester

HRID 1814295Notes

Reaction equation

HRID 1814295 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:42](Cl)(=[O:44])[CH3:43]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:42](=[O:44])[CH3:43])=[CH:21][C:20]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chloride3×HCID 8471TriethylamineHCID 865882033-(4-amino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

Product 1

HCID 225040833-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic tert-butyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 3-(4-amino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (5.56 g, 11.3 mmol) was dissolved in 100 mL methylene chloride, and triethylamine (2.8 mL) is added. One equivalent of acetyl chloride was added and stirred at room temperature. Additional portions of acetyl chloride were added approximately every 30 min until the starting material was consumed. (A total of 1.5 equivalents of acetyl chloride was used over about 2 hours.) The solvent was removed and replaced with ethyl acetate. The organic solution was washed twice with 5% cold HCl, then once with water, once with saturated potassium carbonate, then once with brine. The solution was dried over anhydrous magnesium sulfate, filtered and the solvent removed. The product was chromatographed with 30% chloroform/ethyl acetate, to yield 5.16 g (85%) of 3-(4-acetylamino-2-benzyloxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic tert-butyl ester acid as a yellow foam. 1H NMR (CDCl3) 7.73 (1H, d, J=8.42 Hz), 7.6-7.5 (4H, m), 7.5-7.3 (3H, m), 6.9 (1H, d, J=8.6 Hz), 5.85 (1H, d, J=9.52), 5.3-5.1 (2H, m), 4.8-4.6 (1H, m), 3.56 (3H, s), 2.92 (3H, s), 2.7-2.38 (2H, m), 2.14 (3H, s), 1.40 (9H, s).

Workup

  1. customwas consumed
  2. custom) The solvent was removed
  3. washThe organic solution was washed twice with 5% cold HCl
  4. dry with materialThe solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe product was chromatographed with 30% chloroform/ethyl acetate

Sources & evidence

ORD record
ord-4fa3ee7fdf5c4e08bef2f10d8be34b94
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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