Water → HCID 54162109, compound

HRID 247862Notes

Reaction equation

HRID 247862 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([C:12](=[N:23][OH:24])[CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=1)[CH3:2].CN(C1C=CC=CN=1)C.[C:35](OC(=O)C)(=[O:37])[CH3:36].O>ClCCl.CCOCC>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([C:12](=[N:23][O:24][C:35](=[O:37])[CH3:36])[CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 86746786HCID 86746786, compound

Product 1

HCID 54162109HCID 54162109, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl-4-amino-3-[3'-(N-tert-butyloxycarbonylamino)-1'-hydroxyiminopropyl]benzoate (4.8 g, 14 mmol) and dimethylamino pyridine (1.67 g, 14 mmol) in dichloromethane (200 ml) was added acetic anhydride (1.3 ml, 14 mmol), under an atmosphere of nitrogen. After 2 hours the solution was poured into water (200 ml) and partitioned. The organic layer was separated, washed once more with water (200 ml), then the combined organic phases dried (MgSO4). The solvent was removed in vacuo, to afford an oily solid. Ether (200 ml) was added, and the mixture evaporated in vacuo once more to give a white solid. The solid was taken up in more ether (100 ml) and filtered off, to afford the title compound (4.4 g, 82%) as a white solid. m.p. 130°-135° C. NMR δ (250 MHz, CDCl3) 1.40 (12H, m), 2.27 (3H, s), 3.18 (2 H, t, J=7 Hz), 3.43 (2H, m), 4.33 (2H, q, J=7 Hz), 4.70 (1H, br s), 6.69 (1H, d, J=9 Hz), 7.82 (1H, dd, J=9 and 2 Hz), 8.17 (1H, br s).

Workup

  1. custompartitioned
  2. customThe organic layer was separated
  3. washwashed once more with water (200 ml)
  4. dry with materialthe combined organic phases dried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto afford an oily solid
  7. customthe mixture evaporated in vacuo once more
  8. customto give a white solid
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-811c9cce6f8742dfba2b656fbf8d663d
Source dataset
uspto-grants-1993_05
Patent number
US05208248

Reaction notes

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