Sodium Hydroxide → HCID 19004359, compound

HRID 2225741Notes

Reaction equation

HRID 2225741 reaction equation
C[O:2][C:3](=[O:28])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][CH2:13][NH:14][C:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[O:16])=[CH:7][CH:6]=1.[OH-].[Na+]>O1CCCC1.CO>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[C:15]([NH:14][CH2:13][C:12]#[C:11][C:8]1[CH:7]=[CH:6][C:5]([C:4](=[O:27])[C:3]([OH:28])=[O:2])=[CH:10][CH:9]=1)=[O:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54550459HCID 54550459, compound

Product 1

HCID 19004359HCID 19004359, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[3-[[(2-naphthalenyl)carbonyl]amino]-1-propynyl]-alpha-oxobenzeneacetic acid methyl ester (0.225 g) in tetrahydrofuran (2 mL) and methanol (1 mL) was treated with 1N sodium hydroxide (1 mL). After five minutes, the reaction mixture was concentrated and the resulting white suspension partitioned between dichloromethane (10 mL) and 1N hydrochloric acid (2 mL). The aqueous layer was diluted with saturated sodium chloride and was extracted with tetrahydrofuran (2×10 mL). The combined extracts were dried (MgSO4) and concentrated to give 0.2 g of a white solid, mp 153°-155° C. Crystallization from dichloromethane-ethyl acetate-hexane gave 0.15 g of 4-[[(2-naphthalenyl)carbonyl]amino]-1-propynyl]-alpha-oxobenzeneacetic acid, mp 156-°158° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe resulting white suspension partitioned between dichloromethane (10 mL) and 1N hydrochloric acid (2 mL)
  3. additionThe aqueous layer was diluted with saturated sodium chloride
  4. extractionwas extracted with tetrahydrofuran (2×10 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-471a02c2729c408ba2570bf566893299
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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