Methanol → 4-[6-(2-ethylhexanamido)indole-1-yl-methyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 1904461Notes

Reaction equation

HRID 1904461 reaction equation
[CH2:1]([CH:3]([CH2:28][CH2:29][CH2:30][CH3:31])[C:4]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=2[O:26][CH3:27])=[CH:9][CH:8]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[Cl-].[C:40]1([N+:46]2([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)C=CC=C[CH:47]2C(=O)N)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C[OH:62]>>[C:40]1([N:46]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:47]([O:22][C:21](=[O:23])[C:20]2[CH:24]=[CH:25][C:17]([CH2:16][N:13]3[C:14]4[C:10](=[CH:9][CH:8]=[C:7]([NH:6][C:4](=[O:5])[CH:3]([CH2:1][CH3:2])[CH2:28][CH2:29][CH2:30][CH3:31])[CH:15]=4)[CH:11]=[CH:12]3)=[C:18]([O:26][CH3:27])[CH:19]=2)=[O:62])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 8471TriethylamineHCID 147087144-[6-(2-Ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoic acidHCID 86743117N,N-diphenylcarbamoylpyridinium chloride

Product 1

HCID 147530114-[6-(2-ethylhexanamido)indole-1-yl-methyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydrideYield 79%

Procedure

A solution of the acid (D) (3.1 g) and triethylamine (1.0 ml) in methanol (30 ml) was treated with a solution of N,N-diphenylcarbamoylpyridinium chloride (2.5 g) in methanol (30 ml). The resultant precipitate was collected by filtration, washed with methanol, and dried under vacuum to give 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride (A) as a white solid (3.54 g, 79%); mp 159°-162° C.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with methanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-e1391294c824487d8007b1c836dd51e3
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

Loading…