Hydrochloric Acid → HCID 86742710, compound

HRID 2292356Notes

Reaction equation

HRID 2292356 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([OH:13])[CH:7]=1)=[O:4].CN([Si](C)(C)C)C(=O)C(F)(F)F.[O:26]=[C:27]1[C@@H:30]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:29][NH:28]1.Cl[S:43]([N:46]=[C:47]=[O:48])(=[O:45])=[O:44].C(N(CC)CC)C.COC1C=C(NC(=O)CNC(=O)OCC2C=CC=CC=2)C=CC=1OC.Cl>C(#N)C.C(OCC)(=O)C.ClCCl>[OH:13][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:1][S:43]([NH:46][C:47]([N:28]2[CH2:29][C@H:30]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:27]2=[O:26])=[O:48])(=[O:45])=[O:44])[CH:11]=[CH:10][C:9]=1[OH:12]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 21277152HCID 21277152, compoundHCID 86742709HCID 86742709, compound

Product 1

HCID 86742710HCID 86742710, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 1.24 g (6.79 mmol) of 2-amino-N-(3,4-dihydroxyphenyl)acetamide in 30 ml of absolute acetonitrile was added 2.71 g (13.6 mmol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide. After stirring for two hours, the clear solution was evaporated to dryness, finally at high vacuum at 55° C. The residue was dissolved in 30 ml of ethyl acetate (solution A). To a suspension of 1.5 g (6.79 mmol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 40 ml of ethyl acetate was added 0.96 g (6.79 mmol) of chlorosulfonyl isocyanate. After stirring for one hour, the solution was cooled to 0° C. and 15 ml of dichloromethane and subsequently 2.06 g (20.37 mmol) of triethylamine (dropwise) was added. To this mixture, solution A was added dropwise and after stirring overnight at room temperature, 30 ml of ice water was added. The pH was adjusted to 1 with 3N hydrochloric acid, the phases were separated and the organic phase was dried over sodium sulfate. After the evaporation of the solvent, the residue was triturated with ether, filtered and dried in vacuo; yield: 1.63 g.

Workup

  1. customthe clear solution was evaporated to dryness, finally at high vacuum at 55° C
  2. dissolutionThe residue was dissolved in 30 ml of ethyl acetate (solution A)
  3. stirringAfter stirring for one hour
  4. stirringafter stirring overnight at room temperature
  5. customthe phases were separated
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. customAfter the evaporation of the solvent
  8. customthe residue was triturated with ether
  9. filtrationfiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-4d2b3ba1875a43f9872e4823cafa32a7
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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