Hydrochloric Acid → HCID 15730211, compound

HRID 1461877Notes

Reaction equation

HRID 1461877 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][O:8][CH2:9][C:10]([OH:12])=O)=[O:6])[CH3:3].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[C:29]1([CH2:35][O:36][C:37]2[C:46]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[CH:45][C:44]([S:55]([OH:58])(=[O:57])=[O:56])=[CH:43][C:38]=2[C:39]([NH:41][NH2:42])=[O:40])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>CN(C)C=O.CN(C1C=CN=CC=1)C.O>[CH3:13][C:2]([CH3:1])([O:4][C:5]([NH:7][O:8][CH2:9][C:10]([NH:42][NH:41][C:39](=[O:40])[C:38]1[CH:43]=[C:44]([S:55]([OH:58])(=[O:57])=[O:56])[CH:45]=[C:46]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:37]=1[O:36][CH2:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:12])=[O:6])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 2755974(Boc-aminooxy)acetic acidHCID 15730210HCID 15730210, compound

Product 1

HCID 15730211HCID 15730211, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
-10 °C

Procedure

A solution of [(1,1-dimethylethoxy)carbonyl]aminooxy acetic acid (Example 7b, 1.0g, 5.2 mmole) and N-methylmorpholine (0.57 ml, 5.2 mmole) in 10 ml of dimethylformamide at -10° C. was treated dropwise with isobutylchloroformate (0.74 ml, 5.7 mmole). The mixture was stirred at -10° C. for 1 hour, then was treated with a suspension of 2,3-di(phenylmethoxy)-5-sulfobenzoic acid hydrazide (2.24g, 5.2 mmole) in 20 ml of dimethylformamide followed by the dropwise addition of a solution of N-methylmorpholine (0.86 ml, 7.8 mmole) and 4-(N, N-dimethylamino)pyridine (30 mg) in 10 ml of dimethylformamide over 20 minutes. The reaction was stirred for 1 hour at 0° C., then was allowed to warm to ambient temperatures overnight. Evaporation in vacuo gave an oil which was taken up in 30 ml of water. The pH was adjusted to 2 with aqueous hydrochloric acid and the oily product was extracted into ethyl acetate. Drying over magnesium sulfate and evaporation gave a residue which crystallized with hexane. The solid was filtered and dried to give 2.3g. mp 103°-105° C.

Workup

  1. stirringThe reaction was stirred for 1 hour at 0° C.
  2. temperatureto warm to ambient temperatures overnight
  3. customEvaporation in vacuo
  4. customgave an oil which
  5. extractionthe oily product was extracted into ethyl acetate
  6. dry with materialDrying over magnesium sulfate and evaporation
  7. customgave a residue which
  8. customcrystallized with hexane
  9. filtrationThe solid was filtered
  10. customdried
  11. customto give 2.3g

Sources & evidence

ORD record
ord-dce731e3dafe407fb141b3f336e6c674
Source dataset
uspto-grants-1991_12
Patent number
US05077432

Reaction notes

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