Methanol → HCID 18463927, compound

HRID 2231087Notes

Reaction equation

HRID 2231087 reaction equation
C([O:3][C:4](=[O:32])[CH:5]([N:7]1[C:13](=[O:14])[CH:12]([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[C:21]([Cl:23])[C:20]([O:24][CH2:25][CH:26]=[CH2:27])=[C:19]([Cl:28])[CH:18]=2)[CH2:11][CH2:10][C:9](=[O:30])[N:8]1[CH3:31])[CH3:6])C.CO>[OH-].[Na+].O>[CH2:25]([O:24][C:20]1[C:19]([Cl:28])=[CH:18][C:17]([C:16]([NH:15][CH:12]2[C:13](=[O:14])[N:7]([CH:5]([CH3:6])[C:4]([OH:32])=[O:3])[N:8]([CH3:31])[C:9](=[O:30])[CH2:10][CH2:11]2)=[O:29])=[CH:22][C:21]=1[Cl:23])[CH:26]=[CH2:27]

Participants

5

Reactant 2

HCID 887MethanolHCID 53950544HCID 53950544, compound

Product 1

HCID 18463927HCID 18463927, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-[6-(4-Allyloxy-3,5-dichloro-benzoylamino)-2-methyl-3,7-dioxo-[1,2]diazepan-1-yl]-propionic acid ethyl ester (17) (216 mg, 0.44 mmol) was stirred in 1N NaOH (2 mL) and MeOH (2 mL) at room temperature for 45 min. The mixture was diluted with water (30 mL), extracted with dichloromethane three times. The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to dryness to afford 201 mg (99% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.58-1.68 (m, 3H), 1.88-2.00 (m, 1H), 2.40-2.48 (m, 1H), 2.80-3.18 (m, 2H), 3.25-3.48 (d, 3H), 4.47-4.65 (m, 2.5H), 4.74-4.81 (m, 0.5H), 4.90-5.05 (m, 1H), 5.27-5.31 (d, 1H), 5.38-5.43 (d, 1H), 6.08-61.8 (m, 1H), 7.07-7.22 (m, 2H), 7.71 (d, 2H). Analytical HPLC: 5.85 min. LC-MS (ES+): m/e=458, 460 (M+H+).

Workup

  1. extractionextracted with dichloromethane three times
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-7182bee465fc492bb89a51f114b31c70
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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