N-(tert-butoxycarbonyl)glycine → HCID 69286068, compound

HRID 2225249Notes

Reaction equation

HRID 2225249 reaction equation
[CH:1]([N:4]([CH3:15])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[C@H:7]([CH2:12][O:13][CH3:14])[CH2:6]1)([CH3:3])[CH3:2].[C:16]([O:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>ClCCl.C(OCC)(=O)C>[CH:1]([N:4]([CH3:15])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:25](=[O:26])[CH2:24][NH:23][C:21](=[O:22])[O:20][C:16]([CH3:17])([CH3:18])[CH3:19])[C@H:7]([CH2:12][O:13][CH3:14])[CH2:6]1)([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69285537HCID 69285537, compound

Product 1

HCID 69286068HCID 69286068, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the crude dihydrobromide salt of (1R,3R,4S)-N1-isopropyl-3-(methoxymethyl)-N1-methylcyclohexane-1,4-diamine prepared according to the procedure of Example 4b, Step 2 (270 mg) in dichloromethane (5 mL) was treated with tert-butoxycarbonylaminoacetic acid (126 mg), diisopropylethylamine (0.80 ml) and HATU (516 mg). The mixture was stirred for 3 h at rt. Ethyl acetate and saturated aqueous NaHCO3 were added and the layers were separated. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum to provide tert-butyl 2-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(methoxymethyl)cyclohexylamino)-2-oxoethylcarbamate (185 mg) as a yellow gum, used without further purification. MS found: (M+H)+=372.4.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with additional ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-18126d63cd5245ab87fe82c3b164017d
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

Loading…