Sodium Hydroxide → HCID 19100698, compound

HRID 1974970Notes

Reaction equation

HRID 1974970 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[C:13]([C:14]#[N:15])=[C:12]([S:16][CH3:17])[S:11][C:10]=1[C:18]([O:20]CC)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1>[C:14]([C:13]1[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([C:18]([OH:20])=[O:19])[S:11][C:12]=1[S:16][CH3:17])#[N:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19100752HCID 19100752, compound

Product 1

HCID 19100698HCID 19100698, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 3-bis(t-butoxycarbonyl)amino-4-cyano-5-(methylthio)thiophene-2-carboxylate (10 g, 22 mmol), tetrahydrofuran (250 ml) and 4N sodium hydroxide (25 ml) was heated at 50° C. for 16 hours. The mixture was evaporated, and water (50 ml) was added followed by acidification with acetic acid (pH=4) at 0° C. The precipitate was filtered off and dried to afford 7.05 g (99%) of 4-cyano-5-methylthio-3-(t-butoxycarbonylamino)thiophene -2-carboxylic acid. 1H-NMR (DMSO-D6, δ): 1.45 (s, 9H), 2.70 (s, 3H), 9.20 (s, 1H).

Workup

  1. customThe mixture was evaporated
  2. additionwater (50 ml) was added
  3. customfollowed by acidification with acetic acid (pH=4) at 0° C
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-4209174d6d9e47a9997eda946b9c6a5b
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

Loading…