Diethyl Ether → HCID 66893735, compound

HRID 19367Notes

Reaction equation

HRID 19367 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][CH2:24][O:25][CH3:26])[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:27](OCC)C.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:27][O:21][C:20](=[O:22])[C@@H:19]([NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])[CH2:23][CH2:24][O:25][CH3:26]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 167693TrimethylsilyldiazomethaneHCID 51340500HCID 51340500, compound

Product 1

HCID 66893735HCID 66893735, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

In a flask was placed (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methoxy-butyric acid (500 mg, 1.41 mmol), diethyl ether (20 mL) and methanol (5 mL) and cooled to 0° C. in an ice bath. To this mixture was added a 2M solution of (trimethylsilyl)diazomethane in diethyl ether (1.41 mL, 2.82 mmol) dropwise. The mixture was stirred and warmed to 25° C. The mixture was then concentrated to afford (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methoxy-butyric acid methyl ester (489 mg, 94%) as a white solid.

Workup

  1. customIn a flask was placed
  2. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-8845d0905b144c53818c6598e43aa1e0
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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