Tetrahydrofuran → HCID 178484174, compound

HRID 2355473Notes

Reaction equation

HRID 2355473 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:23][C@H:24]1[CH2:29][CH2:28][C@@H:27](O)[CH2:26][CH2:25]1)[CH2:10][N:11]([CH3:22])[C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[F-].[F:39]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.C1COCC1>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([F:39])[CH2:26][CH2:25]1)[CH2:10][N:11]([CH3:22])[C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 28179Fluoride IonHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 178484177HCID 178484177, compound

Product 1

HCID 178484174HCID 178484174, compoundYield 20%

Procedure

A mixture of benzyl (S)-2-(t-butoxycarbonylamino)-3-(cis-4-hydroxycyclohexyl)-propyl(methyl)carbamate (1 g, 2.38 mmol), base Et3N (5 mL, 28 mmol), a fluoride source NEt3(HF)3 (1.9 mL, 9.52 mmol) and perfluorobutanesulfonyl fluoride (2.1 mL, 9.52 mmol) were stirred in THF (24 mL, 1 mmol/10 mL) in a capped vial or flask at 50° C. until LC revealed complete conversion. The reaction mixture was quenched with water and extracted with EtOAc (2×100 mL), dried over MgSO4, and evaporated. The residue was then purified by preparative HPLC to give benzyl (S)-2-(t-butoxycarbonylamino)-3-(trans-4-fluorocyclohexyl)propyl(methyl)carbamate (200 mg, 20%) as a white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was then purified by preparative HPLC

Sources & evidence

ORD record
ord-38f33762bf854caa88cece523ca6c523
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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