Trifluoroacetic acid → HCID 131716458, compound

HRID 2165285Notes

Reaction equation

HRID 2165285 reaction equation
C(OC([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11]([O:14][CH2:15][C:16]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])[C:10]1=[O:25])=O)(C)(C)C.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>C1(OC)C=CC=CC=1>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[NH2:8][C@H:9]1[CH:12]([CH3:13])[N:11]([O:14][CH2:15][C:16]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])[C:10]1=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86744087HCID 86744087, compound

Product 1

HCID 131716458HCID 131716458, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

(3S-trans)-[[3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinyl]oxy]acetic acid. cyclohexyl ester (2.23 g) prepared analogously to the procedure of example 91A was dissolved in a solution of 25 ml of trifluoroacetic acid and 2.5 ml of anisole at -10° C. The mixture was evaporated in vacuo 25 minutes later and the residue was stirred with ether, filtered off and dried over P2O5 to give colorless crystals of (3S)-[[3-amino-4 methyl2-oxo-1-azetidinyl]oxy]acetic acid, cyclohexyl ester, trifluoroacetate salt (yield 1.53). The salt (1.50 g) was suspended in 30 ml of acetonitrile. MSTFA (2.37 ml) was added at 0° C. and the solution was allowed to stand overnight. After evaporating in vacuo, the residue (1.75 g) was dissolved in dry tetrahydrofuran (25 ml), 1.4 g of (Z)-2-amino-α-methoxyimino)-4-thiazoleacetic acid, 1-hydroxybenzotriazole ester was added and the mixture was stirred at room temperature for 4 hours. Tetrahydrofuran was removed in vacuo at 30° C., the residue was taken up in ether, shaken with ice-cold aqueous NaHCO3 (in) and twice with cold water. The dried ethyl acetate layer was evaporated in vacuo. The resulting oil (2.14 g) chromatographed on silica gel with ethyl acetate to give 1.58 g of the title compound; melting point 85°-90° C. dec.

Workup

  1. customThe mixture was evaporated in vacuo 25 minutes later
  2. filtrationfiltered off
  3. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-3f372cbcf59544279396b05e35ea1721
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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