Dichloromethane → HCID 67661848, compound

HRID 1599139Notes

Reaction equation

HRID 1599139 reaction equation
Cl.[C:2]([CH2:4][C@@H:5]1[CH2:13][C@@H:12]2[C@@H:8]([CH2:9][NH:10][CH2:11]2)[C@@:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])([OH:14])[CH2:6]1)#[N:3].ClCCl.[CH2:26]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][C:41](O)=[O:42])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C)CCCN=C=NCC>O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C>[C:2]([CH2:4][C@@H:5]1[CH2:13][C@@H:12]2[C@@H:8]([CH2:9][N:10]([C:41](=[O:42])[CH2:40][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[O:33][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:11]2)[C@@:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])([OH:14])[CH2:6]1)#[N:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 519916(2-Benzyloxyphenyl)acetic acidHCID 67660461HCID 67660461, compound

Product 1

HCID 67661848HCID 67661848, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178526939HCID 178526939, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

The procedure is as described in Example 4, starting from 1.61 g of (3aS,4S,6S,7aR)-6-cyanomethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride, 50 cm3 of dichloromethane, 0.70 cm3 of triethylamine, 1.21 g of (2-benzyloxyphenyl) acetic acid, 0.02 g of hydroxybenzotriazole hydrate and 1.05 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. Purification by chromatography followed by recrystallization from ethyl acetate give 1.4 g of (3aS,4S,6S,7aR)-6-cyanomethyl-2-[(2-benzyloxyphenyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-ol are obtained in the form of white crystals.

Workup

  1. customPurification by chromatography
  2. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-455698a0cb1d40fab104fc87ddeb81e9
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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