Ethyl Acetate → HCID 86736894, compound

HRID 1701674Notes

Reaction equation

HRID 1701674 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:36])[CH2:34]Br)[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:13]1=[O:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:38][N:39]1[C:43]([SH:44])=[N:42][N:41]=[N:40]1.C(OCC)(=O)C>C1OC1C.CN(C)C=O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:36])[CH2:34][S:44][C:43]2[N:39]([CH3:38])[N:40]=[N:41][N:42]=2)[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:13]1=[O:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 54357627HCID 54357627, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 86736894HCID 86736894, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6378Propylene OxideSolvent

Procedure

To a stirred solution of 563 mg (1 mmol) of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-4-bromo-2-butenoate in a mixture of 2 ml propylene oxide and 4 ml of dimethylformamide at 0° was added 128 mg (1.1 mmol) of 1-methyl-5-mercapto-1,2,3,4-tetrazole. After 1 hour at 0°, the solution was added to a large amount of ethyl acetate and washed thoroughly with brine. The ethyl acetate layer was dried and evaporated to provide the title product: nmr (CDCl3) δ 2.20 and 2.37 (s, 3, CH3), 3.83 and 3.86 (s, 3, N--CH3), 4.43 (s, 2, --CH2S--), 5.88 (d, 2, C4 --H), 5.50 (q, 1, C3 --H), 4.57 (s, 2, side chain CH2) and 7.2 (b, ArH).

Workup

  1. washwashed thoroughly with brine
  2. dry with materialThe ethyl acetate layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-83f2b370b90f4cb9b4ecc5130b5d1350
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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