Chloroform → Ammonium Hydroxide

HRID 745125Notes

Reaction equation

HRID 745125 reaction equation
C(=O)([O:3]C(C)(C)C)[NH2:2].[CH3:9][C:10]([CH3:56])([O:12][C:13]([NH:15][CH:16]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][N:50]2[CH2:55][CH2:54][O:53][CH2:52][CH2:51]2)=[CH:43][CH:42]=1)[CH:17]([OH:39])[CH2:18][NH:19][CH2:20][CH:21]([OH:38])[CH:22]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:14])[CH3:11].C(Cl)(Cl)Cl>CO>[NH4+:2].[OH-:3].[CH3:11][C:10]([CH3:56])([O:12][C:13]([NH:15][CH:16]([CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][CH2:48][CH2:49][N:50]2[CH2:51][CH2:52][O:53][CH2:54][CH2:55]2)=[CH:45][CH:46]=1)[CH:17]([OH:39])[CH2:18][NH:19][CH2:20][CH:21]([OH:38])[CH:22]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:14])[CH3:9]

Participants

6

Reactant 3

HCID 6212Chloroform2×HCID 77922tert-Butyl carbamate2×HCID 78186916HCID 78186916, compound

Product 2

HCID 14923Ammonium HydroxideHCID 78186916HCID 78186916, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Alternatively, Compound 175e was prepared as follows. Compound 174 was converted to the title Compound 175e by a procedure analogous to that used for the synthesis of Compound 21. Flash chromatography (100% CHCl3 to CHCl3 --MeOH--NH4OH: 0:4.5:0.5) on a silica gel column gave Compound 175e as a white solid which was lyophilized from 1,4-dioxane to give a white lyophilate.

Workup

  1. customAlternatively, Compound 175e was prepared

Sources & evidence

ORD record
ord-1c4b9666e6c241a385c0cd96bcb3bcc9
Source dataset
uspto-grants-1996_09
Patent number
US05559256

Reaction notes

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