Acetic Acid → HCID 86691245, compound

HRID 2038225Notes

Reaction equation

HRID 2038225 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:5])[CH3:4].C(O)(=O)C.[F:10][C:11]([F:27])([F:26])[C@@H:12]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:27][C:11]([F:10])([F:26])[C@@H:12]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:13]1[CH:14]=[CH:15][C:16]([CH2:19][NH:1][CH2:2][C@H:3]([OH:5])[CH3:4])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 439938(2R)-1-aminopropan-2-olHCID 5049666Sodium triacetoxyborohydrideHCID 86691246HCID 86691246, compound

Product 1

HCID 86691245HCID 86691245, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (2R)-1-aminopropan-2-ol (0.4 g, 5.33 mmol) in DCM (10.6 mL); then acetic acid (366.2 uL, 6.39 mmol) and N-[(1S)-2,2,2-trifluoro-1-(4-formylphenyl)-ethyl]-methanesulfonamide (1.65 g, 5.86 mmol). Stir the resulting mixture at ambient temperature for 2 hours; then add sodium triacetoxyborohydride (2.82 g, 13.31 mmol); and stir at ambient temperature overnight. Add MeOH (1 mL) and evaporate a portion of the solvent under reduced pressure. Purify via SCX chromatography eluting with 2M NH3/MeOH. Concentrate the appropriate fractions under reduced pressure to give the title compound (1.7 g, 93.8%). MS (m/z): 341 (M+1).

Workup

  1. stirringand stir at ambient temperature overnight
  2. customAdd MeOH (1 mL) and evaporate a portion of the solvent under reduced pressure
  3. customPurify via SCX chromatography
  4. washeluting with 2M NH3/MeOH
  5. concentrationConcentrate the appropriate fractions under reduced pressure

Sources & evidence

ORD record
ord-994f2649dec741989fa391a83fb8b1e8
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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