Formic Acid → Acetic-formic anhydride

HRID 547624Notes

Reaction equation

HRID 547624 reaction equation
[CH:1]([OH:3])=O.[C:4]([O:7][C:8](=[O:10])C)(=[O:6])[CH3:5].[C:11](OC=O)(=O)C.CC([N:21]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][N:39]([CH:47]3[CH2:55][C:54]4[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=4)[CH2:48]3)[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[CH:34][CH:33]=2)=[CH:27][C:26]=1[NH2:56])[C:22](=[O:24])[O-:23])(C)C.O1[CH2:61][CH2:60][CH2:59]C1>>[C:4]([O:7][CH:8]=[O:10])(=[O:6])[CH3:5].[CH2:48]1[C:49]2[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:55][CH:47]1[N:39]([CH2:38][C:35]1[CH:36]=[CH:37][C:32]([O:31][C:28]2[CH:29]=[CH:30][C:25]([NH:21][C:22]([O:23][C:60]([CH3:59])([CH3:61])[CH3:11])=[O:24])=[C:26]([NH:56][CH:1]=[O:3])[CH:27]=2)=[CH:33][CH:34]=1)[C:40](=[O:41])[O:42][C:43]([CH3:45])([CH3:46])[CH3:44]

Participants

7

Reactant 5

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 75269Acetic-formic anhydrideHCID 86628098HCID 86628098, compound

Product 2

HCID 75269Acetic-formic anhydrideHCID 57585871HCID 57585871, compound

Procedure

Formic acetic anhydride was prepared by adding 96% formic acid (1.24 ml, 32.2 mmol) to acetic anhydride (1.52 ml, 16.1 mmol) and stirring for 1 hour. (Ref: Org. Process Research & Development, 2000, 4, p. 567-570). Formic acetic anhydride (0.16 ml, 0.87 mmol) was added to a solution of 1,1-dimethylethyl[2-amino-4-({4-[(2,3-dihydro-1H-inden-2-yl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}oxy)phenyl]carbamate (430 mg, 0.79 mmol) in 20 mL of tetrahydrofuran. The reaction mixture was stirred for 30 minutes then quenched with 2 mL of 1N NaOH and stirred vigorously. The reaction was passed through a Varian Chem Elute™ 1010 tube that was pretreated for five minutes with 2 mL of 1N NaOH. The tube was eluted with ethyl acetate. The eluent was dried over MgSO4 and concentrated to give 1,1-dimethylethyl 2,3-dihydro-1H-inden-2-yl[(4-{[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-(formylamino)phenyl]oxy}phenyl)methyl]carbamate. (M-1) 572.0, 2.93 min (LC/MS method B)

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. customthen quenched with 2 mL of 1N NaOH
  3. stirringstirred vigorously
  4. washElute™ 1010 tube that
  5. waitwas pretreated for five minutes with 2 mL of 1N NaOH
  6. washThe tube was eluted with ethyl acetate
  7. dry with materialThe eluent was dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-30b8c5d458c74a47a0a0e10829f03997
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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