4-Toluenesulfonyl chloride → HCID 86629100, compound

HRID 1863979Notes

Reaction equation

HRID 1863979 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([O:19][C:20]([N:22]1[CH2:27][C@H:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]3[O:38][CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:34]=3[CH:44]=2)[C@@H:25]([C:45]2[CH:50]=[CH:49][C:48]([CH2:51][O:52][CH2:53][C@@H:54]([CH3:58])[CH2:55][O:56][CH3:57])=[CH:47][CH:46]=2)[C@H:24]([CH2:59][OH:60])[CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl.COC(C)(C)C>[CH2:12]([O:19][C:20]([N:22]1[CH2:23][C@@H:24]([CH2:59][O:60][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[C@H:25]([C:45]2[CH:50]=[CH:49][C:48]([CH2:51][O:52][CH2:53][C@@H:54]([CH3:58])[CH2:55][O:56][CH3:57])=[CH:47][CH:46]=2)[C@@H:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]3[O:38][CH2:37][CH2:36][N:35]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[C:34]=3[CH:44]=2)[CH2:27]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 66877910HCID 66877910, compound

Product 1

HCID 86629100HCID 86629100, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

7.077 mmol of 4-methyl-benzenesulfonyl chloride are added to a solution of 6.583 mmol of (3S,4R,5R)-3-hydroxymethyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl) -phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid benzyl ester (Example 1a), 9.875 mmol of triethylamine and 0.329 mmol of dimethyl-pyridin-4-yl-amine in 65 ml of dichloromethane under argon at 0° C. After overnight stirring at room temperature, the reaction mixture is diluted with tert-butyl methyl ether, washed successively with saturated aqueous sodium bicarbonate solution, water and brine, dried with sodium sulfate and evaporated. The crude title compound is obtained as a yellow oil. Rf=0.44 (EtOAc-heptane 2:1); Rt=5.94 (gradient I).

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate solution, water and brine
  2. dry with materialdried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-7add35e94d264b23a3b37aee5d7a3826
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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