Hydrochloric Acid → HCID 22279655, compound

HRID 2086188Notes

Reaction equation

HRID 2086188 reaction equation
C(OC(=O)[C:5]([NH:25][C:26]([O:28][CH3:29])=[O:27])([CH3:24])[CH2:6][CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=1)C.[Cl-].[Li+].[BH4-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:24][C:5]1([CH2:6][CH2:7][C:8]2[S:9][CH:10]=[C:11]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:12]=2)[CH2:29][O:28][C:26](=[O:27])[NH:25]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 69736935HCID 69736935, compound

Product 1

HCID 22279655HCID 22279655, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

2-Methoxycabonylamino-2-methyl-4-[4-(5-phenylpent-1-ynyl)thiophen-2-yl]butanoic acid ethylester (0.82 g, 1.92 mmol) obtained in Example 25(g) was dissolved in a mixture of ethanol (15 ml) and tetrahydrofuran (10 ml), and lithium chloride (0.24 g, 5.75 mmol) and sodium borohydride (0.22 g, 5.75 mmol) were added thereto in an ice bath, and then the reaction mixture was stirred for 2 hours at 70° C. under a nitrogen atmosphere. After the reaction solution was acidified with 1N hydrochloride acid, the resulting solution was extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacua. The residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-1:1) to give the title compound (0.65 g, 96% yield).

Workup

  1. additionwere added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washthe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacua
  6. customThe residue was purified by chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4:1-1:1)

Sources & evidence

ORD record
ord-8ec48586fdac485388128cf6006d9079
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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