Acetic Anhydride → Benzyl tert-butyl [3-(acetylamino)propane-1,2-diyl]biscarbamate

HRID 1504847Notes

Reaction equation

HRID 1504847 reaction equation
[NH2:1][CH2:2][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C(Cl)Cl.C(OCC)(=O)C>[C:31]([NH:1][CH2:2][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86731716Benzyl tert-butyl (3-aminopropane-1,2-diyl)biscarbamate

Product 1

HCID 86731717Benzyl tert-butyl [3-(acetylamino)propane-1,2-diyl]biscarbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl tert-butyl (3-aminopropane-1,2-diyl)biscarbamate (8.0 g, 25 mmol) and triethylamine (7.9 g, 78 mmol) in DCM (100 mL) was added acetic anhydride (2.8 g, 27 mmol) at 0° C. After 1 hour, the reaction mixture was diluted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by chromatography on silica gel to give benzyl tert-butyl [3-(acetylamino)propane-1,2-diyl]biscarbamate. MS ESI calc'd. for C18H28N3O5 [M+H]+ 366. found 366. 1H NMR (400 MHz, CD3OD) δ 7.34-7.30 (m, 5H), 5.01 (s, 2H), 3.59-3.51 (m, 3H), 2.87-2.77 (m, 2H), 2.0 (s, 3H), 1.42 (s, 9H).

Workup

  1. concentrationThe organic layer was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f89a98cc85b543b18cb33b55f2b4f133
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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