Benzoyl chloride → HCID 22258151, compound

HRID 1610993Notes

Reaction equation

HRID 1610993 reaction equation
[C:1]([NH:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:10]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)[C:41]1[CH:46]=[CH:45]C=[CH:43][CH:42]=1>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:1]([NH:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:10]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[C:6]([OH:8])=[O:7])(=[O:3])[C:2]1[CH:45]=[CH:46][CH:41]=[CH:42][CH:43]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10151939HCID 10151939, compound

Product 1

HCID 22258151HCID 22258151, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Example 13 Part A compound (197 mg, 0.4 mmol) under argon at 0-5° C. in THF (1.5 mL) was added triethylamine (0.2 mL, 1.6 mmol), DMAP (2 mg, 0.02 mmol) and benzoyl chloride (70 μL, 0.6 mmol). The reaction mixture was allowed to warm to room temperature and after 15 h, it was diluted with EtOAc, washed once with 10% citric acid, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 161 mg (71% yield). LC/MS gave the correct molecular ion [(M+H)+=564] for the desired compound.

Workup

  1. washwashed once with 10% citric acid
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b2d075cec249440fa14daf6700335230
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

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