Lithium Hydroxide → HCID 131723119, compound

HRID 1699756Notes

Reaction equation

HRID 1699756 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[C:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[N:18][O:19][CH2:20][C:21]([NH:23][CH2:24][C@H:25]([NH:30][C:31]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:32])[C:26]([O:28]C)=[O:27])=[O:22])=[CH:13][CH:12]=1)(=[NH:10])[NH2:9].[Li+].[OH-]>CO>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[C:8]([C:11]1[CH:12]=[CH:13][C:14]([CH:17]=[N:18][O:19][CH2:20][C:21]([NH:23][CH2:24][C@H:25]([NH:30][C:31]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:32])[C:26]([OH:28])=[O:27])=[O:22])=[CH:15][CH:16]=1)(=[NH:9])[NH2:10]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131723120HCID 131723120, compound

Product 1

HCID 131723119HCID 131723119, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[2-[[(4-amidinophenylmethylene)amino]oxy]-1-oxoethylamino]-2-(S)-[n-butyloxycarbonylamino]-propanoate TFA salt (91 mg, 0.17 mmol) was dissolved in 1.5 mL of methanol and 0.51 mL of 1M LiOH was added. After stirring at room temperature for 16 hours, the reaction mixture was evaporated in vacuo and the residue was dissolved in 2 mL of 1:1 CH2Cl2/TFA. This solution was evaporated in vacuo and the residue was purified by preparative HPLC (Dynamax-300A C18 reverse phase column; 21.4×250 mm; 10 ml/min flow rate; 254 nM; gradient: from 100% H2O with 0.05% TFA to 20% H2O and 80% CH3CN with 0.05% TFA in 50 minutes) to yield 63 mg of desired product as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 9.39 (bs, 2H), 9.2 (bs, 2H), 8.44 (s, 1H), 7.99 (t, 1H), 7.83 (m, 4H), 7.36 (d, 1H), 4.6 (s, 2H), 4.05 (m, 1H), 3.9 (m, 2H), 3.55 (m, 1H), 3.36 (m, 1H), 1.46 (m, 2H), 1.3 (m, 2H), 0.85 (t, 3H); MS (ESI): m/e 408.2 (M+H)+; HRMS (FAB), e/z Calc. for (M+H)+: 408.188309, Found: 408.189211.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in 2 mL of 1:1 CH2Cl2/TFA
  3. customThis solution was evaporated in vacuo
  4. customthe residue was purified by preparative HPLC (Dynamax-300A C18 reverse phase column; 21.4×250 mm; 10 ml/min flow rate; 254 nM; gradient: from 100% H2O with 0.05% TFA to 20% H2O and 80% CH3CN with 0.05% TFA in 50 minutes)

Sources & evidence

ORD record
ord-0b7c2c497f6d41819ad21284c8fb064a
Source dataset
uspto-grants-2002_02
Patent number
US06348504B1

Reaction notes

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