Methanol → HCID 178446009, compound

HRID 36530Notes

Reaction equation

HRID 36530 reaction equation
C([S:4][CH2:5][C@H:6]([C:20]([F:23])([F:22])[F:21])[C:7]([NH:9][C@H:10]([C:15]1[NH:19][N:18]=[N:17][N:16]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])(=O)C.[NH4+].[OH-].C(OCC)(=O)C.CO>O>[F:22][C:20]([F:21])([F:23])[C@@H:6]([CH2:5][SH:4])[C:7]([NH:9][C@H:10]([C:15]1[NH:19][N:18]=[N:17][N:16]=1)[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 178477123HCID 178477123, compound

Product 1

HCID 178446009HCID 178446009, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of (S,S)-2-[(acetylthio) methyl]-3,3,3-trifluoro-N-[3-methyl-1-(1H -tetrazol-5-yl)butyl]propanamide [prepared in Example 39(e), 1.034 g., 2.95 mmol.] in 6 mL of degassed water at room temperature under argon was added a mixture of concentrated NH4OH (1.95 mL) and water (1.95 mL). After two minutes, the reaction was quenched with saturated potassium bisulfate (pH 1.5) and extracted with ethyl acetate. The organic extracts were dried and purified by flash chromatography (50 mm×6 inch, 1:1 hexanes:ethyl acetate +0.5% acetic acid) to give 0.76 g. of white solid product. This material was combined with 25 mg. from a previous experiment and recrystallized from ethyl acetate/hexanes to give 0.69 g. of the title (S,S) isomer product as a white solid, m.p. 183°-184° C., TLC Rf =0.14 (1:1, hexanes:ethyl acetate +0.5% acetic acid). [α]D =-39.8° (c=0.57, methanol).

Workup

  1. additionwas added
  2. customthe reaction was quenched with saturated potassium bisulfate (pH 1.5)
  3. extractionextracted with ethyl acetate
  4. customThe organic extracts were dried
  5. custompurified by flash chromatography (50 mm×6 inch, 1:1 hexanes:ethyl acetate +0.5% acetic acid)
  6. customto give 0.76 g
  7. customfrom a previous experiment and recrystallized from ethyl acetate/hexanes
  8. customto give 0.69 g

Sources & evidence

ORD record
ord-e44fb2e8005d4b718501daac95de48df
Source dataset
uspto-grants-1995_05
Patent number
US05414017

Reaction notes

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