Hydrochloric Acid → HCID 13937969, compound

HRID 980584Notes

Reaction equation

HRID 980584 reaction equation
C1(C([O:14][C:15](=[O:44])[CH2:16][O:17]/[N:18]=[C:19](/[C:38]2[N:39]=[C:40]([NH2:43])[S:41][CH:42]=2)\[C:20](=[O:37])[NH:21][CH:22]2[C:25]3([CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:24]([O:31][S:32]([OH:35])(=[O:34])=[O:33])[C:23]2=[O:36])C2C=CC=CC=2)C=CC=CC=1.[K].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.Cl>ClCCl.O.C1(C)C=CC=CC=1>[NH2:43][C:40]1[S:41][CH:42]=[C:38](/[C:19](=[N:18]/[O:17][CH2:16][C:15]([OH:44])=[O:14])/[C:20](=[O:37])[NH:21][CH:22]2[C:25]3([CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[N:24]([O:31][S:32]([OH:35])(=[O:33])=[O:34])[C:23]2=[O:36])[N:39]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 5462222PotassiumHCID 13937967HCID 13937967, compound

Product 1

HCID 13937969HCID 13937969, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

(Z)-[[[1-(2-Amino-4-thiazolyl)-2-oxo-2-[[2-oxo-1-(sulfooxy)-7-oxa-1-azaspiro[3.5]non-3-yl]-amino]ethylidene]amino]oxy]acetic acid diphenylmethyl ester, monopotassium salt (0.39 g, 0.57 mmole) was slurried in 6 ml of dry dichloromethane and 1.5 ml of anisole at -10° C. under argon and treated with 10 ml of trifluoroacetic acid. After 1 hour, dry toluene (12 ml) was added and the volatiles were removed in vacuo at 10° C. The residue was washed twice with hexane, then taken up in water and the pH adjusted to 6.75 with dilute potassium bicarbonate. Chromatography on HP-20 in water gave product mixed with inorganics. The impure product was lyophilized, taken up in water and the pH adjusted to 2.5 with dilute hydrogen chloride. Chromatography on HP-20 in a water-50% acetone:water gradient and lyophilization of the pure product fractions yielded the title compound as a white powder, 177 mg.

Workup

  1. customthe volatiles were removed in vacuo at 10° C
  2. washThe residue was washed twice with hexane
  3. customChromatography on HP-20 in water gave product
  4. additionmixed with inorganics

Sources & evidence

ORD record
ord-8423555aed6c4924959696011062116e
Source dataset
uspto-grants-1987_01
Patent number
US04638060

Reaction notes

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