Triethylamine → HCID 23402052, compound

HRID 1063924Notes

Reaction equation

HRID 1063924 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:32])[CH2:10][C:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[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.C(N(CC)CC)C.[CH3:40][O:41][CH2:42][CH2:43][NH:44][S:45](ON1C(=O)CCC1=O)(=[O:47])=[O:46]>C(#N)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:32])[CH2:10][C@@:11]1([C:20]2[S:21][C:22]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([S:45]([NH:44][CH2:43][CH2:42][O:41][CH3:40])(=[O:47])=[O:46])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22276467HCID 22276467, compoundHCID 22277015N-(2-methoxyethylaminosulfonyloxy)succinimide

Product 1

HCID 23402052HCID 23402052, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2-tetrahydropyranyloxy)-2-[7-(5-(4-chlorophenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (100 mg) and triethylamine (22.3 mg) in acetonitrile (2 ml) was added N-(2-methoxyethylaminosulfonyloxy)succinimide (55.6 mg) and the mixture was stirred at ambient temperature for 1 hour. The mixture was partitioned with ethyl acetate and water. The organic layer was separated, washed with 5% citric acid solution, water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of chloroform and methanol (200:1, 100:1, 200:3) to give N-(2-tetrahydropyranyloxy)-2-[(S)-7-(5-(4-chlorophenyl)-2-thienyl)-4-(2-methoxyethylaminosulfonyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (80.0 mg) as a colorless amorphous powder.

Workup

  1. customThe mixture was partitioned with ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with 5% citric acid solution, water, saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of chloroform and methanol (200:1, 100:1, 200:3)

Sources & evidence

ORD record
ord-4874c208f0104e6db2fd24dc17e84e94
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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