Ammonia → HCID 86613499, compound

HRID 495292Notes

Reaction equation

HRID 495292 reaction equation
C(Cl)(=O)OC.C(N(CC)CC)C.[CH2:13]([C:15]1[C:20]([O:21]C(OC)=O)=[CH:19][C:18]([O:26]C(OC)=O)=[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[C:16]=1[CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH3:14].[BH4-].[Na+].N>CO.O1CCCC1.O>[CH2:13]([C:15]1[C:20]([OH:21])=[CH:19][C:18]([OH:26])=[C:17]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[C:16]=1[CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH3:14]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 86613500HCID 86613500, compound

Product 1

HCID 86613499HCID 86613499, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In the same manner as in Example 118, methyl 2-acetyl-3,5-bis(methoxycarbonyloxy)-6-(3-methoxyphenyl)phenylacetate was obtained from methyl 2-acetyl-3,5-dihydroxy-6-(3-methoxyphenyl)phenylacetate (320 mg, 0.97 mmol) obtained in the above, using methyl chlorocarbonate (0.2 mL, 2.6 mmol), triethylamine (0.4 mL, 2.9 mmol) and tetrahydrofuran (5.0 mL); and from the resulting compound, obtained was methyl 2-ethyl-3,5-bis(methoxycarbonyloxy)-6-(3-methoxyphenyl)phenylacetate, using sodium borohydride (210 mg, 5.5 mmol), water (3.0 mL) and tetrahydrofuran (5.0 mL). Then, the resulting compound was treated with methanol solution (5.0 mL) of 7 mmol/L ammonia to obtain Compound 142 (170 mg, 55%).

Workup

  1. customobtained in the above,
  2. customand from the resulting compound, obtained

Sources & evidence

ORD record
ord-bcd6cf9a530c4b9e8852353e12b57c94
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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