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Hydrochloric Acid → 2-(3-chloro-4,5-dihydro-1,2-oxazol-5-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)acetic acid

HRID 1632353
Notes
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Reaction equation

HRID 1632353 reaction equation
[CH2:1]1[C:5]([Cl:6])=[N:4][O:3][C@@H:2]1[C@H:7]([NH2:11])[C:8]([OH:10])=[O:9].[C:12](=[O:15])(O)[O-:13].[Na+].O[CH2:18][CH:19]1[C:31]2[C:30](C(Cl)=O)=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2.Cl>C(OCC)(=O)C.O>[Cl:6][C:5]1[CH2:1][CH:2]([CH:7]([NH:11][C:12]([O:13][CH2:18][CH:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:15])[C:8]([OH:10])=[O:9])[O:3][N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 294641AcivicinHCID 516892Sodium BicarbonateHCID 86737604HCID 86737604, compound

Product 1

HCID 3323662-(3-chloro-4,5-dihydro-1,2-oxazol-5-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)acetic acid

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To 178 mg. of AT-125 in 4 ml. of water is added 300 mg. of sodium bicarbonate. After cooling the mixture to 0°-5° C., 300 mg. of 9-hydroxymethyl fluorenylcarbonyl chloride is added and it is stirred for two hours and allowed to stand overnight at room temperature. The resulting semi solid is taken up in ethyl acetate and 1N hydrochloric acid is added until a pH of 3 is attained. The organic phase is separated, dried over sodium sulfate, concentrated and chromatographed on 20 g. of CC-4 silica gel employing 40% ethyl acetate/Hexane. Those fractions containing the desired product are evaporated and the residue recrystallized from ethyl acetate to yield 3-chloro-α-[[(9H-fluoren-9-yl-methoxy)carbonyl]amino]-4,5-dihydro-5-isoxazole acetic acid. m.p. 182°-183° C. The NMR fits the desired structure.

Workup

  1. temperatureAfter cooling the mixture to 0°-5° C.
  2. waitto stand overnight at room temperature
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed on 20 g
  7. additionThose fractions containing the desired product
  8. customare evaporated
  9. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-11566fd09ac84e798a53612bf1ec4364
Source dataset
uspto-grants-1984_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04474968

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes