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Potassium Carbonate → Ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate

HRID 1777976
Notes
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Reaction equation

HRID 1777976 reaction equation
[C:1](=[O:17])([O-])[O:2][CH2:3][CH:4](N1C(=O)CCC1=O)[Si:5]([CH3:8])([CH3:7])[CH3:6].[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][NH:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:24])([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][N:28]([C:1]([O:2][CH2:3][CH2:4][Si:5]([CH3:6])([CH3:7])[CH3:8])=[O:17])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:24])([CH3:21])([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4319362Ethyl N-(2-((tert-butoxycarbonyl)amino)ethyl)glycinate2×HCID 866405022,5-Dioxopyrrolidin-1-yl(2-(trimethylsilyl)ethyl) carbonate

Product 1

HCID 131734793Ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

2,5-Dioxopyrrolidin-1-yl(2-(trimethylsilyl)ethyl) carbonate (5.44 g, 20.99 mmol) was added to a mixture of ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)amino)acetate (intermediate 126, 4.70 g, 19.08 mmol) and K2CO3 (5.80 g, 42.0 mmol) in DCM (60 ml) and water (30 ml) at room temperature. The reaction mixture was vigorously stirred for 20 h at room temperature, partitioned between saturated aqueous NaHCO3 solution and DCM, the mixture extracted with DCM (2×), the combined organic layers dried over Na2SO4 and evaporated to give the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 6.71 (d, br, 1H), 4.16-3.93 (m, 6H), 3.30-3.21 (m, 2H), 3.09-3.00 (m, 2H), 1.37 (s, 9H), 1.19 (t, 3H), 0.99-0.94 (m, 1H), 0.90-0.85 (m, 1H), 0.05 (s, 9H).

Workup

  1. custompartitioned between saturated aqueous NaHCO3 solution and DCM
  2. extractionthe mixture extracted with DCM (2×)
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-53f9db24ced64b48a7fe2c1e56b11a32
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266883B2

Reaction notes

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