Hydrochloric Acid → [[1-(2-Amino-4-thiazolyl)-2-[[1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid, diphenylmethyl ester

HRID 2292347Notes

Reaction equation

HRID 2292347 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:16]([O:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=O)[N:6]=1.C(N(CC)CC)C.C1(OP(Cl)(OC2C=CC=CC=2)=O)C=CC=CC=1.[NH2:56][C@H:57]1[CH2:60][N:59]([C:61]([NH:63][S:64]([NH:67][NH:68][C:69]([NH:71][C:72]2[CH:77]=[CH:76][C:75]([OH:78])=[C:74]([OH:79])[CH:73]=2)=[O:70])(=[O:66])=[O:65])=[O:62])[C:58]1=[O:80].C(OCC)(=O)C.Cl>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:11][O:12][C:13]([CH3:14])([CH3:15])[C:16]([O:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:8]([NH:56][CH:57]2[CH2:60][N:59]([C:61]([NH:63][S:64]([NH:67][NH:68][C:69]([NH:71][C:72]3[CH:77]=[CH:76][C:75]([OH:78])=[C:74]([OH:79])[CH:73]=3)=[O:70])(=[O:66])=[O:65])=[O:62])[C:58]2=[O:80])=[O:10])[N:6]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 8857Ethyl Acetate2×HCID 75654Diphenyl chlorophosphateHCID 135359672-Amino-alpha-((2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy)imino)thiazol-4-acetic acidHCID 53662062(S)-3-Amino-1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxoazetidine

Product 1

HCID 86742706[[1-(2-Amino-4-thiazolyl)-2-[[1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoic acid, diphenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-30 °C

Procedure

Into a -30° C. cold mixture of 0.66 g (1.5 mmol) of (Z)-2-amino-α-[[1-(diphenylmethoxycarbonyl)-1-methylethoxy]imino]-4-thiazoleacetic acid in 13 ml of dry dimethylformamide, 0.63 ml (4.5 mmol) of triethylamine was dropped, followed by 0.33 ml (1.5 mmol) of diphenylchlorophosphate. After stirring at -30° C. for 1 hour, 0.42 ml (3.0 mmol) of triethylamine was dropped in, followed by the addition of 0.80 g (1.5 mmol) of (S)-3-amino-1-[[[[2-[[(3,4-dihydroxyphenyl)amino]carbonyl]hydrazino]sulfonyl]amino]carbonyl]-2-oxoazetidine. The mixture was stirred for 2 hours at -10° C. and an additional 2 hours at 0° C. The solvent was removed in vacuo and the residue was taken up in a few ml of ethyl acetate and ice water. The pH of the mixture was corrected to pH=2 the addition of dilute hydrochloric acid. The insoluble material was collected by suction1) and stirred with a few ml of ethyl acetate until it became crystalline; yield after drying in vacuo: 0.31 g. This material was used in the next step without further purification.

Workup

  1. additionwas dropped
  2. stirringThe mixture was stirred for 2 hours at -10° C. and an additional 2 hours at 0° C
  3. customThe solvent was removed in vacuo
  4. customThe insoluble material was collected by suction1) and
  5. customyield
  6. customafter drying in vacuo
  7. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-67bc1040828745be9fd73b0c6a547f28
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

Loading…