Ammonia → HCID 23146987, compound

HRID 495287Notes

Reaction equation

HRID 495287 reaction equation
C(Cl)(=O)OC.C(N(CC)CC)C.[CH2:13]([C:15]1[C:16]([O:40]C(OC)=O)=[CH:17][C:18]([O:35]C(OC)=O)=[C:19]([C:25]2[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=2)[C:28]([O:30][CH3:31])=[O:29])[C:20]=1[CH2:21][CH2:22][O:23][CH3:24])[CH3:14].[BH4-].[Na+].N>CO.O1CCCC1.O>[CH2:13]([C:15]1[C:16]([OH:40])=[CH:17][C:18]([OH:35])=[C:19]([C:25]2[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=2)[C:28]([O:30][CH3:31])=[O:29])[C:20]=1[CH2:21][CH2:22][O:23][CH3:24])[CH3:14]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 23146933HCID 23146933, compound

Product 1

HCID 23146987HCID 23146987, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In the same manner as in Example 118, methyl 3-[5-acetyl-2,4-bis(methoxycarbonyloxy)-6-(2-methoxyethyl)phenyl]benzoate was obtained from Compound 119 (100 mg, 0.30 mmol) obtained in Example 119, using methyl chlorocarbonate (0.05 mL, 0.65 mmol), triethylamine (0.09 mL, 0.65 mmol) and tetrahydrofuran (3.0 mL); and from the resulting compound, obtained was methyl 3-[5-ethyl-2,4-bis(methoxycarbonyloxy)-6-(2-methoxyethyl)phenyl]benzoate, using sodium borohydride (45 mg, 1.2 mmol), water (2.0 mL) and tetrahydrofuran (2.0 mL). Then, the resulting compound was treated with methanol solution (5.0 mL) of 7 mmol/L ammonia to obtain Compound 131 (37 mg, 37%).

Workup

  1. customand from the resulting compound, obtained

Sources & evidence

ORD record
ord-f8d424649d724562aa707984305f9cc5
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

Loading…