Cyclopropanecarboxylic acid → HCID 91168875, compound

HRID 1727165Notes

Reaction equation

HRID 1727165 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.[CH:37]1([C:40](O)=[O:41])[CH2:39][CH2:38]1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.O1CCCC1>[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:40]([CH:37]4[CH2:39][CH2:38]4)=[O:41])=[O:17])[CH2:15][C@@:7]3([OH:36])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 15655Cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86614036HCID 86614036, compound

Product 1

HCID 91168875HCID 91168875, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (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, 100 mg, 0.19 mmol) and 4-dimethylaminopyridine (30 mg, 0.25 mmol) in tetrahydrofuran (10 ml) was added cyclopropanecarboxylic acid (400 mg, 4.7 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (90 mg, 0.58 mmol) and the resulting mixture stirred at room temperature for 18 h. The reaction mixture was passed through a Sepak® cartridge (silica, 1.5 g) to remove insoluble material and the solvent removed in vacuo. The crude product was purified to give the title compound (20 mg, 18%).

Workup

  1. customto remove insoluble material
  2. customthe solvent removed in vacuo
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-18c69ba30e0b4b18a1f15c3b4ac374e6
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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