Benzyloxycarbonylglycine → HCID 69287319, compound

HRID 2225248Notes

Reaction equation

HRID 2225248 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].[CH2:16]([O:23][C:24]([NH:26][CH2:27][C:28](O)=[O:29])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.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(#N)C>[CH:1]([N:4]([CH3:15])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:28](=[O:29])[CH2:27][NH:26][C:24](=[O:25])[O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:7]([CH2:12][O:13][CH3:14])[CH2:6]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14349BenzyloxycarbonylglycineHCID 81531DiisopropylethylamineHCID 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 69287319HCID 69287319, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 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 (423 mg) in acetonitrile (5 mL) was treated with 2-(benzyloxycarbonylamino)acetic acid (259 mg), diisopropylethylamine (0.80 ml) and HATU (516 mg). The mixture was stirred overnight at rt, then was concentrated under vacuum. The residue was purified by reverse phase HPLC followed by lyopholization to provide benzyl 2-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(methoxymethyl)cyclohexylamino)-2-oxoethylcarbamate (192 mg) as a white powder. MS found: (M+H)+=406.3.

Workup

  1. concentrationwas concentrated under vacuum
  2. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-356170b7806e4a7e836a69c6cea3a839
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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