Acetic Anhydride → HCID 57877635, compound

HRID 2266751Notes

Reaction equation

HRID 2266751 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[N:11]([C:12]([C:14]2[N:15]=[C:16]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=3)[CH:18]=2)=[O:13])[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)(=[O:3])[CH3:2].C(OC1C=C(N2C=C(C(N3CCN(C(OCC4C=CC=CC=4)=O)C[C@@H]3CO)=O)N=C2C2C=CC(C)=CC=2)C=CC=1)C.C(N(CC)C(C)C)(C)C.C(OC(=O)C)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:4][CH2:5][C@H:6]1[CH2:7][NH:8][CH2:9][CH2:10][N:11]1[C:12]([C:14]1[N:15]=[C:16]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=2)[CH:18]=1)=[O:13])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86761246HCID 86761246, compoundHCID 86761247HCID 86761247, compound

Product 1

HCID 57877635HCID 57877635, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Step, C: Benzyl (3R)-3-[(acetyloxy)methyl]-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazine-1-carboxylate To a stirred solution of 3.40 g (6.13 mmol) of benzyl (3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-(hydroxymethyl)-piperazine-1-carboxylate from Step B in 60 mL of anhydrous dichloromethane was added 2.30 mL (13.4 mmol) of N,N-diisopropylethylamine, 1.20 ml (12.2 mmol) of acetic anhydride and 4.0 mg (0.30 mmol) of 4-(dimethylamino)-pyridine. The resulting solution was stirred at ambient temperature overnight, quenched with a saturated aqueous ammonium chloride solution (20 mL). The aqueous layer was separated and extracted with dichloromethane (2×75 mL), and the combined organic layers were washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 50 to 75% ethyl acetate in hexanes gradient) to yield the title compound as a colorless foam. LC/MS 597.2 (M+1).

Workup

  1. customquenched with a saturated aqueous ammonium chloride solution (20 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane (2×75 mL)
  4. washthe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 50 to 75% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-27ce1cee76e34c81ae186c9cad83ba8f
Source dataset
uspto-grants-2010_12
Patent number
US07858629B2

Reaction notes

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