Formic Acid → HCID 10381826, compound

HRID 1768149Notes

Reaction equation

HRID 1768149 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[CH:19][CH:18]=2)[C:13]1=[O:32].Cl>O1CCCC1.ClCCl.O.C(N(CC)CC)C>[F:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([N:14]2[CH2:15][CH2:16][C@@H:12]([NH:11][CH:1]=[O:3])[C:13]2=[O:32])=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 69491091HCID 69491091, compound

Product 1

HCID 10381826HCID 10381826, compoundYield 92%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 188 mg (18 mmol) of acetic anhydride and 107 mg (23 mmol) of formic acid is prepared at 0° C., thereafter, heated to 60° C. for 2 hours. After cooling to RT, the mixture is diluted with 1 ml of tetrahydrofurane and a solution of 213 mg (7 mmol) of (R)-3-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one in 2 ml of dichloromethane, beforehand prepared from the corresponding hydrochloride by treatment with triethylamine, is added. After the addition a white suspension is formed which is stirred at RT for 1 hour. For the working-up, the reaction mixture is treated with dichloromethane and water, then, the organic layer is separated, dried over sodium sulfate and evaporated. There are obtained 215 mg (92% of theory) of (R)-N-{1-[4-(3-Fluoro-benzyloxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-formamide as a white solid; MS: m/e=329 (M+H)+.

Workup

  1. customis prepared at 0° C.
  2. temperatureAfter cooling to RT
  3. additionis added
  4. additionAfter the addition a white suspension
  5. customis formed which
  6. customthe organic layer is separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-4ca9a9ec798241159249d2f6c388d7aa
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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