Acetic Anhydride → HCID 57847067, compound

HRID 550295Notes

Reaction equation

HRID 550295 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:12]2[CH2:13][CH2:14][N:15]([C:16]([C@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[NH:24][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:17])[C@H:11]2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4]1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>O1CCCC1>[C:33]([NH:1][CH2:2][C@H:3]1[C@H:12]2[CH2:13][CH2:14][N:15]([C:16]([C@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[NH:24][C:25](=[O:32])[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:17])[C@H:11]2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4]1)(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57847156HCID 57847156, compound

Product 1

HCID 57847067HCID 57847067, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (163 mg, 0.377 mmol) synthesized in Example 73 in tetrahydrofuran (3 ml) was added acetic anhydride (0.179 ml, 1.88 mmol) under ice-cooling, and the mixture was stirred at room temperature for 10 min. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to column chromatography using basic silica gel and eluted with hexane-ethyl acetate (8:2-0:1, v/v) to give the title compound (117 mg, 60%) as an amorphous form.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (8:2-0:1

Sources & evidence

ORD record
ord-67d262c5927f4c19abcd7a0c87656d38
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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