monoMethyl succinate → HCID 86614041, compound

HRID 1727169Notes

Reaction equation

HRID 1727169 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.[CH3:37][O:38][C:39](=[O:45])[CH2:40][CH2:41][C:42](O)=[O:43].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[C:42]([O:35][C@@H:20]1[C:21]([CH3:34])=[CH:22][C@@H:23]2[C@:28]([OH:29])([C@H:27]([CH3:30])[CH2:26][CH2:25][C@@H:24]2[C:31]([CH3:33])=[CH2:32])[C@H:19]1[O:18][C:16]([C@H:14]1[NH:13][C@@H:8]2[O:9][N:10]([CH3:12])[C:11]3[C:2]([Cl:1])=[CH:3][CH:4]=[CH:5][C:6]=3[C@:7]2([OH:36])[CH2:15]1)=[O:17])(=[O:43])[CH2:41][CH2:40][C:39]([O:38][CH3:37])=[O:45]

Participants

6

Reactant 3

HCID 77487monoMethyl succinateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86614036HCID 86614036, compound

Product 1

HCID 86614041HCID 86614041, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture 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), commercially available 4-(methyloxy)-4-oxobutanoic acid (50 mg, 0.38 mmol), 4-dimethylaminopyridine (60 mg, 0.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (90 mg, 0.58 mmol) and dichloromethane (5 ml) was stirred for 18 h and the reaction mixture concentrated in vacuo. The crude product was purified by chromatography on a Biotage® 12M column eluting with dichloromethane:diethyl ether (4:1). The pure fractions were combined and the solvent removed in vacuo to give the title product (23 mg, 18%).

Workup

  1. concentrationthe reaction mixture concentrated in vacuo
  2. customThe crude product was purified by chromatography on a Biotage® 12M column
  3. washeluting with dichloromethane:diethyl ether (4:1)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d9eb9b2f9d2041fe8b519ce84d43b8ec
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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