Acetoxyacetic acid → HCID 91188657, compound

HRID 1727171Notes

Reaction equation

HRID 1727171 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[OH:35])=[O:17])[CH2:15][C@@:7]3([OH:36])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:37]([O:40][CH2:41][C:42](O)=[O:43])(=[O:39])[CH3:38].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.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[O:35][C:42](=[O:43])[CH2:41][O:40][C:37](=[O:39])[CH3:38])=[O:17])[CH2:15][C@@:7]3([OH:36])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 83766Acetoxyacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86614036HCID 86614036, compound

Product 1

HCID 91188657HCID 91188657, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To (1S,2R,4aS,5R,8R,8aR)-2,8a-dihydroxy-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 139, 210 mg, 0.4 mmol) and 4-dimethylaminopyridine (65 mg, 0.53 mmol) in dichloromethane (10 ml) was added (acetyloxy)acetic acid (60 mg, 0.51 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (90 mg, 0.58 mmol). The resultant mixture was stirred at room temperature and upon completion was concentrated in vacuo. The crude product was purified by chromatography on a Biotage® 12M column eluting with hexane:ethyl acetate (2:1). The pure fractions were combined and the solvent removed in vacuo to give the title product (150 mg, 61%).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe crude product was purified by chromatography on a Biotage® 12M column
  3. washeluting with hexane:ethyl acetate (2:1)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-04c92a56529846688c9bef23808687ec
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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