Di-tert-butyl dicarbonate → HCID 54181390, compound

HRID 850593Notes

Reaction equation

HRID 850593 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][CH2:7][CH2:8][CH2:9][C:10]1([CH3:15])[O:14][CH2:13][CH2:12][O:11]1)[CH3:2].[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O>C1COCC1.CN(C1C=CN=CC=1)C.C(N(CC)CC)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:17])[CH2:7][CH2:8][CH2:9][C:10]1([CH3:15])[O:14][CH2:13][CH2:12][O:11]1)[CH3:2]

Participants

6

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 11791061HCID 11791061, compound

Product 1

HCID 54181390HCID 54181390, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-4 (24 g, 0.104 mol) in 100 mL THF were added a trace of DMAP, 20 drops of triethylamine, and BOC2O (23.8 g, 0.109 mol). After 4 h, evaporative removal of the solvent gave 2-5 as a colorless oil. TLC Rf =0.38 (silica, 30% ethyl acetate/hexane). 1H NMR (300 MHz, CDCl3, mixture of rotamers) δ 4.22 (m, 3H), 3.93 (m, 4H), 3.27 (m, 2H), 1.63 (m, 4H), 1.51 (s, 3H), 1.47 (s, 3H), 1.42 (s, 3H), 1.31 (s, 3H), 1.28 (m, 4H).

Workup

  1. customremoval of the solvent

Sources & evidence

ORD record
ord-f99acbe1100b4b7a90df0fbcc4139c35
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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