Diazomethane → HCID 68441200, compound

HRID 2246949Notes

Reaction equation

HRID 2246949 reaction equation
[N+](=[CH2:3])=[N-].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[C@@H:17]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]4[O:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[C:24]=4[CH:34]=3)[CH2:16][N:15]([S:35]([C:38]3[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[C@@H:14]([CH2:45][C:46]([OH:48])=[O:47])[CH2:13]2)=[CH:8][CH:7]=1>CCOCC.CO>[CH3:3][O:47][C:46](=[O:48])[CH2:45][C@H:14]1[CH2:13][C@H:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:11][CH:10]=2)[C@@H:17]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]3[O:28][CH2:27][CH2:26][N:25]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[C:24]=3[CH:34]=2)[CH2:16][N:15]1[S:35]([C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=1)(=[O:36])=[O:37]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 68439434HCID 68439434, compound

Product 1

HCID 68441200HCID 68441200, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

4 ml of a solution of diazomethane in ether (0.2M) are added dropwise to a solution of 0.12 g of [(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetic acid (from example 25f) in 2 ml of methanol at 0° C. The reaction mixture is worked up after 3.5 hours by quenching with solid magnesium sulfate to decompose any excess diazomethane, filtering and concentrating under reduced pressure to afford the crude title compound as a pale yellow solid with was used in the next step without any further purification. Rf=0.78 (EtOAc); Rt=5.26.

Workup

  1. customby quenching with solid magnesium sulfate
  2. filtrationfiltering
  3. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-a680b06b19004a08a6be41cd3dd28c8e
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

Loading…