Water → HCID 23402030, compound

HRID 1063932Notes

Reaction equation

HRID 1063932 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.[CH:34]1([CH:40]=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C([BH3-])#N.[Na+].O>C(O)C.C(O)(=O)C>[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]([CH2:40][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 16275CyclohexanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23402065HCID 23402065, compound

Product 1

HCID 23402030HCID 23402030, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a 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 cyclohexanecarbaldehyde (46 mg) in ethanol were added sodium cyanoborohydride (26 mg) and acetic acid (1 drop) in an ice-water bath. After 1 hour stirring, to the reaction mixture was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water twice and brine, dried over magnesium sulfate and evaporated. The residue was purified by flash silica gel chromatography eluting with hexane-ethyl acetate=5-1, 2-1, 1-2 to give N-(2-tetrahydropyranyloxy)-2-[(S)-4-(cyclohexylmethyl)-7-(5-(4-ethylphenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (91 mg) as colorless amorphous.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water twice
  3. dry with materialbrine, dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash silica gel chromatography
  6. washeluting with hexane-ethyl acetate=5-1, 2-1, 1-2

Sources & evidence

ORD record
ord-3a66282a3c29461c9033cfc9d716c9f4
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

Loading…