Hydrochloric Acid → HCID 67423285, compound

HRID 1160184Notes

Reaction equation

HRID 1160184 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C:9]1([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:13][CH2:12][O:11][CH:10]1[O:14][CH2:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([N:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:27][CH2:28][CH3:29])[CH:25]=1)[C:19]([O:21]C)=[O:20].[Li+].[OH-].Cl>C1COCC1.CO>[NH2:8][C:9]1([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:13][CH2:12][O:11][CH:10]1[O:14][CH2:15][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([N:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:27][CH2:28][CH3:29])[CH:25]=1)[C:19]([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 131728378HCID 131728378, compound

Product 1

HCID 67423285HCID 67423285, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-{[(3-amino-3-benzyltetrahydrofuran-2-yl)oxy]methyl}-5-[(methylsulfonyl)(propyl)amino]benzoate TFA salt (40 mg, 0.07 mmol) in THF (0.5 mL) and MeOH (0.5 mL) is 1N LiOH (0.6 mL, 0.6 mmol) and the reaction mixture is stirred at RT for 3 h. 1N HCl (0.4 mL, 0.4 mmol) is added and the reaction mixture is concentrated in vacuo to give 3-{[(3-amino-3-benzyltetrahydrofuran-2-yl)oxy]methyl}-5-[(methylsulfonyl)(propyl)amino]benzoic acid as a white solid, used as is in the following coupling.

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-bccd78d4ed184ecd879cb24e0b7c4326
Source dataset
uspto-grants-2010_10
Patent number
US07816378B2

Reaction notes

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