Acetyl chloride → HCID 178473946, compound

HRID 1728481Notes

Reaction equation

HRID 1728481 reaction equation
[C:1]1([S:7][C@@H:8]2[NH:11][C:10](=[O:12])[C@H:9]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[N:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:50](Cl)(=[O:52])[CH3:51]>C1COCC1>[C:1]1([S:7][CH:8]2[N:11]([C:50](=[O:52])[CH3:51])[C:10](=[O:12])[CH:9]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[N:18][C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178523912HCID 178523912, compound

Product 1

HCID 178473946HCID 178473946, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a -78° C. THF (7 mL) solution of compound 14 (450 mg, 0.82 mmol) was added 1N THF solution of sodium bis(trimethylsilyl)amide (0.8 mL) dropwise. The resultant solution was stirred for 10 min, followed by the addition of acetyl chloride (0.054 mL, 0.76 mmol). The resultant solution was warmed to room temperature and stirred for an additional 30 min and concentrated- The residue was partitioned between ethyl acetate and H2O. The organic phase was dried (MgSO4) and concentrated to afford 450 mg (93%, crude yield) of the title compound which was directly used in Step B.

Workup

  1. customTo a -78° C
  2. customconcentrated- The residue was partitioned between ethyl acetate and H2O
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customto afford

Sources & evidence

ORD record
ord-339b8467aa9f4d588f4ebf7fcc878e60
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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