Acetic Acid → (R)-tert-Butyl 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

HRID 598880Notes

Reaction equation

HRID 598880 reaction equation
[CH3:1][C:2]1([CH3:32])[O:7][C:6](=[O:8])[CH:5]([C:9](=O)[C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[C:4](=[O:31])[O:3]1.C(O)(=O)C.[BH4-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:32])[O:3][C:4](=[O:31])[CH:5]([CH2:9][C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=2)[C:6](=[O:8])[O:7]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 57950484(S)-tert-Butyl 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-oxo-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 57950499(R)-tert-Butyl 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-1-oxo-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (22.0 g, 48 mmol) in 200 mL DCM was cooled to −5° C. Acetic acid (32 g, 527 mmol) was added in one portion and sodium tetrahydroborate (4.5 g, 120 mmol) as a solid was added portion wise over about 40 minutes. The reaction mixture was stirred for another 40 minutes and the reaction mixture was stored in the freezer overnight and was then washed with brine (3×150 mL) and water (2×100 mL). The organic layer was dried over MgSO4. The desired product was obtained as a white amorphous solid (21.0 g, 98%). No further purification was performed and the reaction was carried on to the next step.

Workup

  1. additionwas added portion wise over about 40 minutes
  2. customwas stored in the freezer overnight
  3. washwas then washed with brine (3×150 mL) and water (2×100 mL)
  4. dry with materialThe organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-988a214e692a413d8190a9403e8f62a2
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

Loading…