Trifluoroacetic acid → HCID 178460210, compound

HRID 2292342Notes

Reaction equation

HRID 2292342 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:48]/[O:49][CH2:50][CH:51]([C:53]([OH:55])=[O:54])[CH3:52])/[C:8]([NH:10][C@H:11]2[CH2:14][N:13]([C:15]([NH:17][S:18]([NH:21][C:22]3[C:27]([OH:28])=[C:26]([OH:29])[CH:25]=[CH:24][C:23]=3[CH2:30][C:31]([O:33]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:32])(=[O:20])=[O:19])=[O:16])[C:12]2=[O:47])=[O:9])[N:6]=1.C1(OC)C=CC=CC=1.[F:64][C:65]([F:70])([F:69])[C:66]([OH:68])=[O:67]>ClCCl>[F:64][C:65]([F:70])([F:69])[C:66]([OH:68])=[O:67].[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:48]/[O:49][CH2:50][CH:51]([C:53]([OH:55])=[O:54])[CH3:52])/[C:8]([NH:10][C@H:11]2[CH2:14][N:13]([C:15]([NH:17][S:18]([NH:21][C:22]3[C:27]([OH:28])=[C:26]([OH:29])[CH:25]=[CH:24][C:23]=3[CH2:30][C:31]([OH:33])=[O:32])(=[O:19])=[O:20])=[O:16])[C:12]2=[O:47])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 178460209HCID 178460209, compound

Product 1

HCID 178460210HCID 178460210, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 10.83 g (13.6 mmol) of the crude [[[[[(S)-3-[[(Z)-(2-amino-4-thiazolyl)[(2-carboxy-2-methylethoxy)imino]acetyl]amino]-2-oxo-1-azetidinyl]carbonyl]amino]sulfonyl]amino]-3,4-dihydroxybenzeneacetic acid, diphenylmethyl ester in 45 ml of dry dichloromethane at -10° C., a cold solution of 11 ml of anisole in 110 ml of trifluoroacetic acid was added. After being stirred at 0° C. for 10 minutes, the clear solution was evaporated in vacuo at 0°-5° C. and the residue was treated with dry ether. The solid was collected by suction, washed with dry ether, dried in vacuo to give 7.28 g of impure [[[[[(S)-3-[[(Z)-(2-amino-4-thiazolyl)[(2-carboxy-2-methylethoxy)imino]acetyl]amino]-2-oxo-1-azetidinyl]carbonyl]amino]sulfonyl]amino]-3,4-dihydroxybenzeneacetic acid, trifluoroacetate salt.

Workup

  1. customthe clear solution was evaporated in vacuo at 0°-5° C.
  2. additionthe residue was treated with dry ether
  3. customThe solid was collected by suction
  4. washwashed with dry ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bf767defe7964b1c8875609ddc0ee1c6
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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