Methylamine hydrochloride → HCID 57892988, compound

HRID 2242424Notes

Reaction equation

HRID 2242424 reaction equation
[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:2]([C:9](O)=[O:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.CN.[CH3:22][N:23](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OC([C@@H]1C[C@@H](O)C[C@H]1C(=O)N[C@]1(C(OCC)=O)C[C@H]1C=C)=O)(C)(C)C>>[C:15]([O:14][C:12](=[O:13])[NH:1][C@@H:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[C:9](=[O:10])[NH:23][CH3:22])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 4

HCID 6364545Methylamine hydrochlorideHCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59165438(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl ester

Product 1

HCID 57892988HCID 57892988, compoundYield 76%

Procedure

Boc-Chg-OH (387 mg, 1.50 mmol) was coupled to methylamine hydrochloride (111 mg, 1.65 mmol) using the same HATU coupling conditions as in the synthesis of compound 34. The crude product was extracted with EtOAc, washed with brine and concentrated. Purification by flash column chromatography (EtOAc) provided compound 37 (307 mg, 76%) as a colorless solid.

Workup

  1. extractionThe crude product was extracted with EtOAc
  2. washwashed with brine
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (EtOAc)

Sources & evidence

ORD record
ord-af32a8b3658e400fa7496aefb505df68
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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