Methanol → HCID 58155399, compound

HRID 2264655Notes

Reaction equation

HRID 2264655 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[C:14]([O:27][CH3:28])[CH:13]=1)[CH2:6][CH:7]1[CH2:9][CH2:8]1.[CH2:30]([NH2:32])[CH3:31].C[Al](C)C.CO>C1(C)C=CC=CC=1.O1CCCC1.CCCCCCC>[F:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:5]([CH2:6][CH:7]2[CH2:8][CH2:9]2)[CH2:4][C:3]([NH:32][CH2:30][CH3:31])=[O:2])=[CH:13][C:14]=1[O:27][CH3:28]

Participants

8

Reactant 4

HCID 887MethanolHCID 6341EthylamineHCID 16682925TrimethylaluminumHCID 59596848HCID 59596848, compound

Product 1

HCID 58155399HCID 58155399, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

105 mg (0.26 mmol) of 2-[[2-[4-(3-fluoro-benzyloxy)-3-methoxy-phenyl]-ethyl]-(cyclopropylmethyl)amino]-acetic acid methyl ester were dissolved in 5 ml of dry toluene. 0.5 ml of a 2 M (1 mmol) solution of ethylamine in tetrahydrofuran were added at 0° C., followed by 0.4 ml (0.8 mmol) of a 2 M solution of trimethyl aluminium in heptane. The reaction was stirred for 4 hours at room temperature. The solution was cooled to 0° C. and poured into methanol. The solvent was removed and the crude product was purified by flash chromatography (ethyl acetate/hexane 0:100→85:15 gradient v:v) to obtain 52 mg (48% yield) of the title compound as a hygroscopic solid.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customThe solvent was removed
  3. customthe crude product was purified by flash chromatography (ethyl acetate/hexane 0:100→85:15 gradient v:v)

Sources & evidence

ORD record
ord-241fcda60f764edd85e87b706da9f669
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

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