Hydrochloric Acid → HCID 86614036, compound

HRID 1727217Notes

Reaction equation

HRID 1727217 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@H:23]([C@H:24]([C:31]([CH3:33])=[CH2:32])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:34])[C@H:20]4[O:35]C(=O)C)=[O:17])[CH2:15][C@@:7]3([OH:39])[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.CCCCCC>CO.ClCCl>[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@H:23]([C@H:24]([C:31]([CH3:33])=[CH2:32])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:34])[C@H:20]4[OH:35])=[O:17])[CH2:15][C@@:7]3([OH:39])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 86614034HCID 86614034, compound

Product 1

HCID 86614036HCID 86614036, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of (1S,2R,4aS,5R,8R,8aR)-2-(acetyloxy)-8a-hydroxy-3,8-dimethyl-5-(1-methylethenyl)-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 1, 1 g) in methanol (25 ml) was added a solution of concentrated hydrochloric acid (2 ml) in methanol (25 ml). After 5 days the reaction mixture was diluted with dichloromethane (150 ml), washed with water (3×100 ml), filtered through cotton wool and evaporated to dryness to give a yellow, oily solid. This residue was partially dissolved in dichloromethane (25 ml) and hexane (50 ml) was slowly added. After 1 hour, the suspension was filtered to give the product as an off-white solid (900 mg).

Workup

  1. washwashed with water (3×100 ml)
  2. filtrationfiltered through cotton wool
  3. customevaporated to dryness
  4. customto give a yellow, oily solid
  5. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-0e5e391ad0464e28894aae4d38b952b4
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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