HCID 69338924, compound → HCID 69736006, compound

HRID 2086196Notes

Reaction equation

HRID 2086196 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([CH3:29])[CH2:7][CH:8]([NH:25][C:26](=[O:28])[CH3:27])[C:9]1[S:10][C:11]([C:14]#[C:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][CH2:5][C@H:6]([CH3:29])[CH2:7][CH:8]([NH:25][C:26](=[O:28])[CH3:27])[C:9]1[S:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 69338924HCID 69338924, compound

Product 1

HCID 69736006HCID 69736006, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2R)-Acetylamino-2-methyl-4-[5-(5-phenylpent-1-ynyl)thiophen-2-yl]butyl acetate (337 mg, 0.82 mmol) obtained in Example 49(a) was dissolved in methanol (17 ml), and 10% palladium-charcoal (170 mg) was added thereto followed by stirring for 16 hours under a hydrogen atmosphere. After the catalyst was filtered out through Celite, the filtrate was evaporated to dryness under reduced pressure to give (2R)-acetylamino-2-methyl-4-[5-(5-phenylpentyl)thiophen-2-yl]butyl acetate (318 mg, 93% yield). The obtained (2R)-acetylamino-2-methyl-4-[5-(5-phenylpentyl)thiophen-2-yl]butyl acetate (298 mg, 0.72 mmol) was dissolved in 6 ml of a mixture solvent (tetrahydrofuran:methanol:water=1:1:1), and lithium hydroxide monohydrate (301 mg, 7.17 mmol) was added thereto followed by stirring for 6 hours at 50° C. The reaction solution was poured into water, extracted with ethyl acetate, and after the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo. The residue (243 mg) was dissolved in methanol, and oxalic acid (65 mg, 0.72 mmol) was added thereto to precipitate crystals. The crystals were filtered off to afford the title compound (251 mg, 83% yield) as white crystals.

Workup

  1. filtrationAfter the catalyst was filtered out through Celite
  2. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-614ac5e5a22c4a15a8839f889c398a57
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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