Trimethylsilyldiazomethane → (R)-Methyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoate

HRID 526812Notes

Reaction equation

HRID 526812 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[O:7])([CH3:4])[CH3:3].[Si](C=[N+]=[N-])(C)(C)[CH3:19]>C(Cl)Cl.CO>[NH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:15]([O:17][CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 7018770Boc-D-Lys-OH

Product 1

HCID 29926888(R)-Methyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoateYield 98.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-α-Boc-D-lysine 12 (1.00 g, 4.06 mmol) in CH2Cl2 (20 mL) and MeOH (5.0 mL) was charged with TMS-diazomethane [(CH3)3SiCHN2 0.6 M solution in hexane, 13.5 mL, 8.12 mmol] at 0° C. and stirred at the same temperature for 1 h and at room temperature for another 1 h. The solvent was removed under reduced pressure to afford crude product 14 (1.04 g, crude) as a yellow oil, which was directly used for the next step without further purification: 1H NMR (400 MHz, CD3OD) δ 4.12-4.05 (m, 1H), 3.70 (s, 3H), 2.62 (t, J=7.0 Hz, 2H), 1.82-1.70 (m, 1H), 1.69-1.58 (m, 1H), 1.54-1.32 (m, 4H), 1.43 (s, 9H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3837ad1ad89044ad991bb40472935a61
Source dataset
uspto-grants-2016_05
Patent number
US09346753B2

Reaction notes

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