Sodium Hydroxide → HCID 19747374, compound

HRID 484455Notes

Reaction equation

HRID 484455 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[C:18]([O:17][C:15]([NH:14][CH2:13][CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:22])=[O:2])=[CH:6][CH:7]=1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54305385HCID 54305385, compound

Product 1

HCID 19747374HCID 19747374, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-(Tertiarybutoxycarbonylamino)propyl)phenylacetic acid methyl ester (2.0 g) was dissolved in 50% aqueous methanol (100 ml) with sodium hydroxide (1 g) and stirred at room temperature for 14 h. The methanol was removed under vacuum and the residual aqueous solution was acidified to pH1 using 1N hydrochloric acid, and the resulting precipitate extracted into ethyl acetate (2×100 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum to give the required product as a white solid (1.82 g). δ (360 MHz, CDCl3) 1.44 (9H, s, COC(CH3)3, 1.78 (2H, m, CH2CH2CH2NH), 2.60 (2H, t, J=7.5 Hz, CH2CH2CH2NH), 3.13 (2H, m, CH2CH2CH2NH), 3.60 (2H, s, CH2CO2H), 4.57 (1H, br, s, NH), 7.12 (2 H, d, J=8.0 Hz, ArH), 7.19 (2H, d, J=8.0 Hz, ArH); m/e (CI) 294 (M+1).

Workup

  1. customThe methanol was removed under vacuum
  2. extractionthe resulting precipitate extracted into ethyl acetate (2×100 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2d38c452aa854f74b44408dd2b1d6645
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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