Methanol → HCID 86737994, compound

HRID 1577496Notes

Reaction equation

HRID 1577496 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][N:11]([C@H:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=2)[C:14]([OH:16])=[O:15])[C:10]1=[O:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:32]1([C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N+]=[N-])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(Cl)(Cl)Cl.CO>O1CCOCC1.CC(O)=O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][N:11]([C@H:13]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=2)[C:14]([O:16][CH:38]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:15])[C:10]1=[O:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 22817349HCID 22817349, compound

Product 1

HCID 86737994HCID 86737994, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2 g (4.49 mmols) of (3S)-3-tert.-butoxycarbonylamino-(αR)-α-(4-tert.-butoxycarbonyloxyphenyl)-2-oxo-1-azetidineacetic acid are dissolved in 50 ml of dioxan and 1 g (5.2 mmols) of diphenyldiazomethane is added all at once to this solution. After 4 hours no further starting material can be seen in the TLC (CHCl3 : MeOH:HOAc, 85:12:3). The red colour is removed by adding two drops of glacial acetic acid and the mixture is evaporated in vacuo at a bath temperature of 25°. The colourless foam is dissolved in 20 ml of absolute ethanol and the product starts to crystallise out. 2.4 g (87% of theory) of pure diphenylmethyl (3S)-3-tert.-butoxycarbonylamino-(αR)-α-(4-tert.-butoxycarbonyloxyphenyl)-2-oxo-1-azetidineacetate with a melting point of 155°-157° are obtained.

Workup

  1. customThe red colour is removed
  2. additionby adding two drops of glacial acetic acid
  3. customthe mixture is evaporated in vacuo at a bath temperature of 25°
  4. dissolutionThe colourless foam is dissolved in 20 ml of absolute ethanol
  5. customto crystallise out

Sources & evidence

ORD record
ord-bb1027d697d0447a95442a985c44d7af
Source dataset
uspto-grants-1981_09
Patent number
US04288364

Reaction notes

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