Sodium Carbonate → HCID 86731707, compound

HRID 1504827Notes

Reaction equation

HRID 1504827 reaction equation
[NH2:1][CH2:2][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][O:5][CH2:6][CH3:7].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C1COCC1.O>[CH2:6]([O:5][CH2:4][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:2][NH:1][C:23](=[O:24])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 86731706HCID 86731706, compound

Product 1

HCID 86731707HCID 86731707, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl (1-amino-3-ethoxypropan-2-yl)carbamate (0.45 g, 2.6 mol) and sodium carbonate (0.29 g, 3.2 mol) in THF (5 mL) and water (3 mL) was added dropwise benzyl chloroformate (0.58 g, 3.4 mol) at 0° C. and then the reaction mixture was allowed to warm to ambient temperature. After 3 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to give benzyl tert-butyl (3-ethoxypropane-1,2-diyl)biscarbamate. MS ESI calc'd. for C18H29N2O5 [M+H]+ 353. found 353. 1H NMR (400 MHz, CD3OD) δ 7.36-7.35 (m, 5H), 5.09 (s, 2H), 3.52-3.49 (m, 1H), 3.42-3.32 (m, 6H), 1.45 (s, 9H), 1.19 (t, J=7.0 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)

Sources & evidence

ORD record
ord-b25f352a6c5d476bb655e866d8588b1e
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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