Acetic Anhydride → HCID 68855307, compound

HRID 916555Notes

Reaction equation

HRID 916555 reaction equation
[NH2:1][CH:2]([CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][C:25]([CH3:27])=[N:24][C:23]=2[CH:28]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(N(CC)CC)C>[C:29]([NH:1][CH:2]([CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][C:25]([CH3:27])=[N:24][C:23]=2[CH:28]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[O:31])[CH3:30]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 68855493HCID 68855493, compound

Product 1

HCID 68855307HCID 68855307, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of tert-butyl 4-[2-amino-3-(2-methylbenzothiazol-5-yloxy)propyl]-piperazinecarboxylate (260 mg) and 4-dimethylaminopyridine (3 mg) in methylene chloride (6 ml) and triethylamine (178 μl) at 0° C. was added acetic anhydride (160 mg), and the mixture allowed to warm to room temperature. After stirring overnight, the mixture was partitioned between methylene chloride and water, and solvent removed from the organic layer under reduced pressure. The residue was chromatographed on a silica gel column, eluting with 25% ethyl acetate/hexanes followed by 10% methanol/methylene chloride, to provide crude tert-butyl 4-[2-(acetylamino)-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinecarboxylate, which was purified by preparative TLC.

Workup

  1. customthe mixture was partitioned between methylene chloride and water, and solvent
  2. customremoved from the organic layer under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b93c2947b1fb4a7d87b74b550b740413
Source dataset
uspto-grants-2007_09
Patent number
US07271169B2

Reaction notes

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