Acetic Acid → HCID 23402068, compound

HRID 1063934Notes

Reaction equation

HRID 1063934 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.[S:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[CH:39]=O.C([BH3-])#N.[Na+].C(O)(=O)C>C(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]([CH2:39][C:35]2[S:34][CH:38]=[CH:37][CH:36]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23402065HCID 23402065, compound

Product 1

HCID 23402068HCID 23402068, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 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 (70.0 mg) and 2-thiophenecarbaldehyde (19.1 mg) in ethanol (1 ml) was added sodium cyanoborohydride (10.7 mg) and a drop of acetic acid at 0° C. The resulting mixture was stirred for 3 hours at room temperature. The reaction was quenched by the addition of saturated sodium bicarbonate (1 ml), and the solvent was evaporated off. The residue was dissolved in ethyl acetate (20 ml), and washed with water, brine, dried over magnesium sulfate, and evaporated. Silica gel column chromatography [eluent: acetone/chloroform (10:1)] afforded N-(2-tetrahydropyranyloxy)-2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-4-(2-thienylmethyl)-1,4-thiazepin-7-yl]acetamide (74.4 mg) as a colorless oil.

Workup

  1. customat 0° C
  2. customThe reaction was quenched by the addition of saturated sodium bicarbonate (1 ml)
  3. customthe solvent was evaporated off
  4. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-cbb06328927347719beb7b56c461e484
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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