Triethylamine → Boc-Lys(Z)-OtBu N-Phenylmethoxycarbonyl

HRID 1752858Notes

Reaction equation

HRID 1752858 reaction equation
[NH2:1][CH:2]([CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(N(CC)CC)C.[C:32]([O:36][C:37](ON1C(=O)CCC1=O)=[O:38])([CH3:35])([CH3:34])[CH3:33]>CN(C)C=O>[CH2:18]([O:17][C:15]([NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:2]([NH:1][C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])[C:3]([O:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:4])=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83168Carbonic acid, 1,1-dimethylethyl 2,5-dioxo-1-pyrrolidinyl esterHCID 2831134Tert-butyl 2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate

Product 1

HCID 66986344Boc-Lys(Z)-OtBu N-Phenylmethoxycarbonyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 2-amino-6-benzyloxycarbonylamino-hexanoate (1.0 g, 2.68 mmol) was dissolved in N,N-dimethylformamide (50 mL) and then triethylamine (5.35 mmol, 0.75 mL) followed by N-(tert-butoxycarbonyloxy)succinimide (0.72 g, 3.35 mmol) was added to the solution. The mixture was stirred overnight and then concentrated. The product was purified from the residue by silica gel chromatography (20% MeOH/chloroform) to give tert-butyl 6-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoate. The tri-protected product was reduced on a Parr hydrogenator (50 psi) to remove the benzyloxycarbonyl protecting group. The solvents were removed to give tert-butyl 6-amino-2-tert-butoxycarbonylamino-hexanoate (0.65 g, 80%).

Workup

  1. additionwas added to the solution
  2. concentrationconcentrated
  3. customThe product was purified from the residue by silica gel chromatography (20% MeOH/chloroform)

Sources & evidence

ORD record
ord-9a76bbc8928141f7a0898e46b8324796
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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