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Sodium Hydroxide → HCID 67365596, compound

HRID 217939
Notes
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Reaction equation

HRID 217939 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:8][CH:7]=1>C1COCC1>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]([OH:24])=[O:4])=[CH:11][CH:10]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 673674894-(4-tert-Butoxycarbonylaminobutyl)benzoic acid methyl ester

Product 1

HCID 67365596HCID 67365596, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

An aqueous (10 mL) solution of sodium hydroxide (0.53 g, 13.18 mmol) was added into the solution of 25 (1.35 g, 4.39 mmol) in THF (60 mL) and the resulting solution was stirred at room temperature for 48 h and at 60° C. for 14 h. Then the solvent was removed under reduced pressure. Water (20 mL) was added and pH was adjusted to 7 with HCl. The white solid precipitate was filtered off, washed with water and dried under vacuum. 1.22 g (95%) of white solid 26 was obtained. 1H NMR (300 MHz, DMSO-d6) δ 1.39 (br s, 11H), 1.52 (m, 2H), 1.64 (m, 2H), 2.92 (m, 2H), 6.84 (m, 1H), 7.28 (d, 2H), 7.85 (d, 2H).

Workup

  1. customThen the solvent was removed under reduced pressure
  2. additionWater (20 mL) was added
  3. filtrationThe white solid precipitate was filtered off
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1d7c69cf13824d6a8528ad6eb1834502
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198286B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes