Sodium Hydroxide → 6-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid

HRID 249629Notes

Reaction equation

HRID 249629 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:24])[CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[OH-].[Na+]>CO>[CH2:17]([O:16][C:14]([NH:13][CH2:12][CH2:11][C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2])=[O:24])=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 692961146-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid methyl ester

Product 1

HCID 692965966-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound 36 was prepared using General Procedure A with ester 35 (3.20 g, 9.13 mmol) and an aqueous NaOH solution (1.46 g, 36.53 mmol in 40 mL of H2O) in MeOH (40 mL). Recrystallization from MeOH produced the desired acid 36 in 95% (2.92 g) yield as a white solid. 1H NMR (CDCl3): δ 7.32 (m, 5H, ArH), 6.10 (s, 1H, NH), 5.67 (s, 1H, NH), 5.04 (s, 2H, OCH2Ar), 3.45 (dt, J=6.4, 12.0 Hz, 2H, CH2NHCO), 3.21 (dt, J=6.4, 12.8 Hz, 2H, CH2NHCO), 2.40 (dt, J=6.0, 6.4 Hz, 2H, CH2CO), 2.32 (t, J=7.2 Hz, 2H, CH2CO), 1.61 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.33 (m, 2H, CH2); ESI-MS m/z 371[M+Cl]−, 359[M+Na]+, 337[M+H]+, 335[M−H]−.

Workup

  1. customThe compound 36 was prepared
  2. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-54d682a6b1bc444dbeb90db8e1f94eb9
Source dataset
uspto-grants-2011_01
Patent number
US07862807B2

Reaction notes

Loading…