Methylamine hydrochloride → HCID 57892988, compound

HRID 1822430Notes

Reaction equation

HRID 1822430 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: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

4

Reactant 3

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)

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 7. The crude product was extracted with EtOAc, washed with brine and concentrated. Purification by flash column chromatography (EtOAc) provided the title compound (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-e4a6c1e96fd1432b9d01682bc4f8e34a
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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