Water → HCID 178471980, compound

HRID 621725Notes

Reaction equation

HRID 621725 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[F:8][C:9]([F:20])([F:19])[C:10](O[C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:11].[CH3:21][CH2:22][O:23][C:24]([CH3:26])=[O:25].[CH2:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[OH2:33].[CH3:34][CH2:35][O:36][CH2:37][CH3:38]>>[OH2:11].[CH2:6]([NH:3][C:4]([CH2:5][C:37]([O:36][CH2:35][CH3:34])=[O:33])=[C:26]([C:13](=[O:18])[C:14]([F:15])([F:16])[F:17])[C:24]([O:23][CH2:22][CH3:21])=[O:25])[C:7]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:27]=1.[CH2:22]([O:23][C:24](=[O:25])[C:26]([C:10](=[O:11])[C:9]([F:20])([F:19])[F:8])=[C:1]([NH:3][CH2:6][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:34][C:35]([O:36][CH2:37][CH3:38])=[O:33])[CH3:21]

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 178471980HCID 178471980, compoundYield 72%

Conditions

Temperature
0 °C

Procedure

To a 3 L 4-necked RB-flask equipped with mechanic stirrer, internal thermomemter, dropping funnel and nitrogen gas inlet was placed 252.7 g (0.87 mol) of product of Step A and 132 ml (96.1 g, 0.95 mol) of triethylamine in 1 L of anhydrous Et2O. This solution was cooled to 0° C. and 129 ml (191.7 g, 1.0 mol) of trifluoroacetic anhydride was added dropwise at such a rate that reaction temperature remained below 10° C. The reaction mixture was stirred at 0° C. for one-half hour and then warmed to room temperature slowly. This reaction was followed by TLC (10% EtOAc/cyclohexane) and usually was completed in 3 to 10 hours. When no more starting material was observed by TLC the mixture was poured into H2O and extracted twice with Et2O. The Et2O layer was dried (MgSO4) and solvent removed in vacuo affording a yellow solid. Crude solid was washed with hexane and dried in vacuo affording 240.84 g (72%) of product as a yellow solid; mp 63°-65° C.

Workup

  1. customTo a 3 L 4-necked RB-flask equipped with mechanic stirrer
  2. customthat reaction temperature
  3. customremained below 10° C
  4. temperaturewarmed to room temperature slowly
  5. extractionextracted twice with Et2O
  6. dry with materialThe Et2O layer was dried (MgSO4) and solvent
  7. customremoved in vacuo
  8. customaffording a yellow solid
  9. washCrude solid was washed with hexane
  10. customdried in vacuo

Sources & evidence

ORD record
ord-935c3f2cff99497a89b958eb788a18c6
Source dataset
uspto-grants-1989_04
Patent number
US04824954

Reaction notes

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