Triphenylphosphine → HCID 53823634, compound

HRID 2225851Notes

Reaction equation

HRID 2225851 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH2:19][CH2:20][OH:21])[S:17][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1.[CH2:26]([O:28][C:29](=[O:39])[C:30]([C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)=[O:31])[CH3:27].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:26]([O:28][C:29](=[O:39])[C:30](=[O:31])[C:32]1[CH:37]=[CH:36][C:35]([O:21][CH2:20][CH2:19][CH2:18][C:16]2[S:17][C:13]3[N:12]4[C:22]([CH3:25])=[N:23][N:24]=[C:11]4[CH2:10][N:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:14]=3[CH:15]=2)=[CH:34][CH:33]=1)[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 19004524HCID 19004524, compound

Product 1

HCID 53823634HCID 53823634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 15, 4-(-2-chlorophenyl)-2-(3-hydroxy-1-propyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (0.322 g) was treated with 4-hydroxyphenylglyoxylic acid ethyl ester (0.168 g) in the presence of diethyl azodicarboxylate (0.155 g) and triphenylphosphine (0.227 g) in dichloromethane (23 mL). The crude ester, isolated in the usual manner, was purified by flash chromatography over silica gel (150 g; ethanol-dichloromethane; 3.5:96.5) to furnish 0.354 g of 4-[3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl] propoxy]-alpha-oxobenzcneacetic acid ethyl ester as a white foam.

Workup

  1. customThe crude ester, isolated in the usual manner
  2. customwas purified by flash chromatography over silica gel (150 g; ethanol-dichloromethane; 3.5:96.5)
  3. customto furnish 0.354 g of 4-[3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl] propoxy]-alpha-oxobenzcneacetic acid ethyl ester as a white foam

Sources & evidence

ORD record
ord-b2ce18c34d834226acecfb087f24704c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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