Triphenylphosphine → HCID 178525420, compound

HRID 1289402Notes

Reaction equation

HRID 1289402 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH2:11][CH2:10]1.[CH2:29]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:43]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:44](O)=[O:45])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O>O1CCCC1>[CH2:29]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:43]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][O:53][CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:44]([O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:14][CH2:13]1)=[O:45])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 189208392,2-Bis(6-benzyloxyhexyl)acetic acidHCID 86599450N-ethoxycarbonyliminocarbamateHCID 178520594HCID 178520594, compound

Product 1

HCID 178525420HCID 178525420, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

First, 3 g of 2,3-difluoro-1-[trans-4-(13-hydroxytridecyl)cyclohexyl]benzene, 3 g of 2,2-bis(6-benzyloxyhexyl)acetic acid, 2.2 g of triphenylphosphine, and 30 ml of tetrahydrofuran were placed in a 100 ml flask. Then, 1.5 g of ethyl azodicarboxylate was added dropwise to the reaction mixture under ice water cooling. The reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to obtain 5.4 g of 13-[trans-4-(2,3-difluorophenyl)cyclohexyl]tridecyl 2,2-bis(6-benzyloxyhexyl)acetate (Y: 97%). The compound thus obtained had a purity of 93.7% by HPLC.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-685ff8f05552457184677eb8e5651e4b
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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