Formic Acid → HCID 53878604, compound

HRID 1701676Notes

Reaction equation

HRID 1701676 reaction equation
CN(C)C(=N)N(C)C.[CH:9]([OH:11])=[O:10].[O:12]([CH2:19][C:20]([NH:22][CH:23]1[CH2:26][N:25]([C:27](=[C:44]([CH3:47])[CH2:45]Br)[C:28]([O:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[C:24]1=[O:48])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[O:12]([CH2:19][C:20]([NH:22][CH:23]1[CH2:26][N:25]([C:27](=[C:44]([CH3:47])[CH2:45][O:11][CH:9]=[O:10])[C:28]([O:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[C:24]1=[O:48])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 664601,1,3,3-TetramethylguanidineHCID 54357627HCID 54357627, compound

Product 1

HCID 53878604HCID 53878604, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.65 ml (5 mmol) of tetramethyl guanidine and 0.15 ml (5 mmol) of formic acid in 20 ml of methylene chloride at 0° was added 563 mg (1 mmol) of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-4-bromo-2-butenoate. The reaction mixture was stirred for 15 minutes at 0° and 2 hours at room temperature. Methylene chloride (100 ml) was added. The resulting solution was washed with brine (3X), dried, and evaporated in vacuo to dryness to provide the title product: nmr (CDCl3) δ 2.17 and 2.05 (s, 3, CH3), 4.92 (m, 2, --CH2O--), 3.60 (m, 2, C4 --H), 4.98 (m, 1, C3 --H), 4.48 (s, 2, side chain CH2), 7.2 (b, ArH) and 8.03 (s, 1, --OCHO).

Workup

  1. washThe resulting solution was washed with brine (3X)
  2. customdried
  3. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-3ecaa9bcaedb49cfbbefa2cc19364e0e
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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