Methanol → HCID 11238729, compound

HRID 270000Notes

Reaction equation

HRID 270000 reaction equation
[ClH:1].O1CCOCC1.C(OC(=O)[N:14]([CH2:37][CH:38]([OH:50])[CH:39]([OH:49])[C:40]1[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=1)[CH2:15][CH2:16][NH:17][S:18]([C:21]1[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][C:27]=2[CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:30]=1)(=[O:20])=[O:19])(C)(C)C.CO>C(Cl)Cl>[ClH:1].[ClH:1].[OH:50][CH:38]([CH:39]([OH:49])[C:40]1[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=1)[CH2:37][NH:14][CH2:15][CH2:16][NH:17][S:18]([C:21]1[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][C:27]=2[CH:28]=[C:29]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:30]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 69313304HCID 69313304, compound

Product 1

HCID 11238729HCID 11238729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 4M HCl/dioxane solution (400 μL, 1.60 mmol) to a solution of [2,3-dihydroxy-3-(4-nitro-phenyl)-propyl]-[2-(7-phenyl-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (100 mg, 0.16 mmol in CH2Cl2 (3 mL) and CH3OH (2 mL) at room temperature under argon, and stir the mixture for 2 hours. Evaporate the solvent and wash the salt several times with Et2O and dry, to obtain the title compound. 1H NMR (CD3OD): δ9.95 (bs, 1H), 8.94-9.12 (m, 3H), 8.78 (m, 1H), 8.24 (m, 2H), 7.94 (m, 2H), 7.52-7.72 (m, 5H); 4.82-4.97 (m, 1H, under H2O signal), 4.07-4.15 (m, 1H), 3.05-3.31 (m, 6H).

Workup

  1. customEvaporate the solvent
  2. washwash the salt several times with Et2O
  3. customdry

Sources & evidence

ORD record
ord-e7c917fc96b148f497f69074440a4a57
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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