Methanol → HCID 21076923, compound

HRID 1374862Notes

Reaction equation

HRID 1374862 reaction equation
C[O:2][C:3]([C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([C@@:19]([N:23]([CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:24]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[O:25])([CH3:22])[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:44])=[O:4].CO.[OH-].[K+]>C1COCC1>[CH2:12]([N:9]1[C:10](=[O:11])[C:5]([C:3]([OH:4])=[O:2])=[C:6]([CH3:44])[N:7]=[C:8]1[C@@:19]([N:23]([CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)=[O:25])([CH3:22])[CH2:20][CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 69021338HCID 69021338, compound

Product 1

HCID 21076923HCID 21076923, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyl-2-{(R)-[(3-tert-butoxycarbonylamino-propyl)-(1-p-tolyl-methanoyl)-amino]-methyl-propyl}-4-methyl-6-oxo-1,6-dihydro-pyrimdine-5-carboxylic acid methyl ester (2.75 g, 4.55 mmol) in THF (60 mL) was added MeOH (30 mL) followed by 1N KOH (18.2 mL, 18.2 mmol). The resultant solution was heated to 60° C. for 3 h, then concentrated under reduced pressure. The residue was diluted with H2O (75 mL), adjusted to pH˜7 with 1N HCl, and extracted with EtOAc (3×75 mL). The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give 2.69 g (100%) of 1-benzyl-2-{(R)-[(3-tert-butoxycarbonylamino-propyl)-(1-p-tolyl-methanoyl)-amino]-methyl-propyl}-4-methyl-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid as an oil which was used in the subsequent step without purification: MS (ES) m/e 591.4 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with H2O (75 mL)
  3. extractionextracted with EtOAc (3×75 mL)
  4. dry with materialThe extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e397ea17ff345639b638d260e5732dd
Source dataset
uspto-grants-2007_01
Patent number
US07166595B2

Reaction notes

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