Methanol → HCID 67080673, compound

HRID 655575Notes

Reaction equation

HRID 655575 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([C@H:19]([C:30](OCC)=[O:31])[CH2:20][CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][C@H:12]1[CH3:35])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].CO.S([O-])(O)(=O)=O.[K+]>O1CCCC1.C(OCC)(=O)C.CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([C@H:19]([CH2:30][OH:31])[CH2:20][CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][C@H:12]1[CH3:35])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 516920Potassium bisulfateHCID 4148881Lithium borohydride2×HCID 67080690HCID 67080690, compound

Product 1

HCID 67080673HCID 67080673, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3.90 g (8.10 mmol) of (R)-4-((S)-3-benzyloxy-1-ethoxycarbonyl-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester in 73 ml of tetrahydrofuran was treated at 0° C. with 4.44 ml (8.90 mmol, 2 M solution in tetrahydrofuran) of lithium borohydride. The reaction was stirred 10 min at 0° C. and 4 h at room temperature, again treated with 3.64 ml (7.30 mmol, 2 M solution in tetrahydrofuran) of lithium borohydride. After 16 h, 5.2 ml of methanol was added and the reaction was neutralized with cold 10% aq. potassium hydrogensulfate solution and extracted with ethyl acetate (3×). The organic phases were washed with 10% aq. potassium hydrogensulfate solution, 10% aq. sodium chloride solution, dried over Na2SO4 and evaporated to yield after flash silica gel column (ethyl acetate/n-heptane 1:1 to ethyl acetate, then ethyl acetate/methanol 98:2) 2.33 g (65%) of the title compound as off-white oil. MS: 441.4 (MH+).

Workup

  1. waitAfter 16 h
  2. extractionextracted with ethyl acetate (3×)
  3. washThe organic phases were washed with 10% aq. potassium hydrogensulfate solution, 10% aq. sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto yield after flash silica gel column (ethyl acetate/n-heptane 1:1 to ethyl acetate

Sources & evidence

ORD record
ord-8345a33c70a949ed938e91710039517e
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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