Triethylamine → HCID 22276629, compound

HRID 1063894Notes

Reaction equation

HRID 1063894 reaction equation
Cl.[O:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[S:17][C:16]([C:18]4([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[S:24](=[O:26])(=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)=[CH:5][N:4]=[CH:3]1.C(N(CC)CC)C.Cl[C:43]([O:45][CH2:46][CH:47]1[C:59]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[C:53]2[C:48]1=[CH:49][CH:50]=[CH:51][CH:52]=2)=[O:44]>C(Cl)(Cl)Cl.CN(C)C=O>[CH:58]1[C:59]2[CH:47]([CH2:46][O:45][C:43]([N:21]3[CH2:20][CH2:19][C:18]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:16]4[S:17][C:13]([C:10]5[CH:9]=[CH:8][C:7]([C:6]6[O:2][CH:3]=[N:4][CH:5]=6)=[CH:12][CH:11]=5)=[CH:14][CH:15]=4)[S:24](=[O:26])(=[O:25])[CH2:23][CH2:22]3)=[O:44])[C:48]3[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:54]=2[CH:55]=[CH:56][CH:57]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 22277046HCID 22277046, compound

Product 1

HCID 22276629HCID 22276629, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a mixture of tert-butyl 2-(7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate hydrochloride (4.2 g) and triethylamine (2.43 g) in a mixture of chloroform (24 ml) and N,N-dimethylformamide (12 ml) was added dropwise a solution of 9-fluorenylmethyl chloroformate (2.28 g) in chloroform (5 ml) under ice-cooling. After being stirred for 30 minutes, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with water, a saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo to give tert-butyl 2-[4-(9-fluorenylmethoxycarbonyl)-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetate (5.8 g) as an amorphous powder.

Workup

  1. temperaturecooling
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with water
  5. dry with materiala saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-01ee8073beac4a099ff76bd9efcad3f8
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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