Oxalic Acid → HCID 20721228, compound

HRID 1063453Notes

Reaction equation

HRID 1063453 reaction equation
[NH2:1][CH:2]([OH:23])[C@H:3]([CH3:22])[CH2:4][CH2:5][C:6]1[S:7][C:8]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:9][CH:10]=1.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CO>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[NH2:1][CH:2]([OH:23])[C@H:3]([CH3:22])[CH2:4][CH2:5][C:6]1[S:7][C:8]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 20721229HCID 20721229, compound

Product 1

HCID 20721228HCID 20721228, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R)-Acetylamino-2-methyl-4-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]butyl acetate (1.40 g 3.40 mmol) obtained in Example 49 (a) was dissolved in 14 ml of a mixture solution (tetrahydrofuran:methanol:water=1:1:1), and lithium hydroxide monohydrate (1.43 g, 34.0 mmol) was added thereto followed by stirring for 4 hours at 50° C. The reaction solution was poured into water, extracted with dichloromethane, and after the dichloromethane layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column (elution solvent; dichloromethane:methanol:ammonia water=20:1:0-10:1:0.1) to afford (2R)-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]butan-1-ol (1.11 g, 100% yield). The obtained (2R)-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]butan-1-ol (360 mg, 1.10 mmol) was dissolved in methanol, and oxalic acid (99 mg, 1.10 mmol) was added thereto to precipitate crystals. The crystals were recrystallized from methanol to afford the title compound (394 mg, 86% yield) as white crystals.

Workup

  1. customto precipitate crystals
  2. customThe crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-fae159083c814e1eb22f789690f1ac2c
Source dataset
uspto-grants-2005_11
Patent number
US06964976B2

Reaction notes

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