Acetic Acid → HCID 23402072, compound

HRID 1063933Notes

Reaction equation

HRID 1063933 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:33])[CH2:10][C@@:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH3:34][C:35]1[N:40]=[C:39]([CH:41]=O)[CH:38]=[CH:37][CH:36]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(O)C.CCCCCC.CC(C)=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:33])[CH2:10][C@@:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([CH2:41][C:39]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:34])[N:40]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23402065HCID 23402065, compound

Product 1

HCID 23402072HCID 23402072, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21880519Acetone hexaneSolvent

Procedure

To the solution of N-(2-tetrahydropyranyloxy)-2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (100 mg) and 6-methylpyridine-2-carbaldehyde (49.2 mg) in ethanol (5 ml) was added sodium triacetoxyborohydride (81.6 mg) and a drop of acetic acid. The resulting mixture was stirred for 1 hour at room temperature. The solvent was evaporated and the residue was partitioned into ethyl acetate (20 ml)/water (20 ml). The organic layer was washed with brine (20 ml), dried over magnesium sulfate, and evaporated to give a yellow gum. Silica gel column chromatography (eluent: acetone hexane (2:3)] was performed to give N-(2-tetrahydropyranyloxy)-2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-4-[(6-methylpyridin-2-yl)methyl]-1,4-thiazepin-7-yl]acetamide (85.9 mg) as a yellowish solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned into ethyl acetate (20 ml)/water (20 ml)
  3. washThe organic layer was washed with brine (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a yellow gum

Sources & evidence

ORD record
ord-09f5dce46658465aafaee23db4b541bd
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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