Allyl chloroformate → HCID 10031568, compound

HRID 1727168Notes

Reaction equation

HRID 1727168 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3].[Cl:8][C:9]1[C:18]2[N:17]([CH3:19])[O:16][C@H:15]3[NH:20][C@H:21]([C:23]([O:25][C@@H:26]4[C@:35]5([OH:36])[C@@H:30]([C@H:31]([CH:38]([CH3:40])[CH3:39])[CH2:32][CH2:33][CH:34]5[CH3:37])[CH:29]=[C:28]([CH3:41])[CH:27]4[OH:42])=[O:24])[CH2:22][C@@:14]3([OH:43])[C:13]=2[CH:12]=[CH:11][CH:10]=1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:8][C:9]1[C:18]2[N:17]([CH3:19])[O:16][C@H:15]3[NH:20][C@H:21]([C:23]([O:25][C@@H:26]4[C@:35]5([OH:36])[C@@H:30]([C@H:31]([CH:38]([CH3:39])[CH3:40])[CH2:32][CH2:33][C@H:34]5[CH3:37])[CH:29]=[C:28]([CH3:41])[C@H:27]4[O:42][C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3])=[O:24])[CH2:22][C@@:14]3([OH:43])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 18052Allyl chloroformateHCID 86614040HCID 86614040, compound

Product 1

HCID 10031568HCID 10031568, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Allyl chloroformate (17.4 mg) was added to a stirred, cooled (0° C.) solution of (1S,4aS,5S,8aR)-2,8a-dihydroxy-3,8-dimethyl-5-(1-methylethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Preparation 144, 50 mg) and 4-dimethylaminopyridine (35 mg) in dichloromethane (5 ml) under an atmosphere of nitrogen. After 30 minutes, the reaction was allowed to warm to room temperature over 15 hours. The reaction mixture was diluted with dichloromethane (25 ml), washed with aqueous citric acid (10% w/w, 3×15 ml) and dried (MgSO4). After evaporation of solvent in vacuo, the residue was purified by flash column chromatography on silica (5 g) eluting with 1:1 ethyl acetate:hexane to give the product (44 mg, 76%).

Workup

  1. washwashed with aqueous citric acid (10% w/w, 3×15 ml)
  2. dry with materialdried (MgSO4)
  3. customAfter evaporation of solvent in vacuo
  4. customthe residue was purified by flash column chromatography on silica (5 g)
  5. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-f2a5ed5f1eaa4da0abd7e9a8ad2d4770
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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