Water → HCID 12811391, compound

HRID 2417774Notes

Reaction equation

HRID 2417774 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C:17](=O)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([SH:23])[CH2:21][SH:22].B(F)(F)F.CCOCC.O>C(O)(=O)C.C(OCC)(=O)C.CCOCC>[CH2:1]([O:8][C:9]([N:11]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:16][C:17]2([S:23][CH2:20][CH2:21][S:22]2)[CH2:18]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 11076282N-Carbobenzyloxy-4-keto-L-proline

Product 1

HCID 12811391HCID 12811391, compoundYield 79.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 1-benzyloxycarbonyl-4-keto-(S)-proline (15.7 g, 60 mmol) in acetic acid (45 ml) and ethyl acetate (45 ml), add 1,2-ethanedithiol (6.2 g, 66 mmol) and stir under nitrogen. Add boron trifluoride etherate (redistilled) and stir 4 hours. Pour the reaction mixture into a mixture of water (175 ml) ethyl acetate (120 ml) and ether (60 ml). Wash the organic layer with water (3×175 ml) then extract twice with 1.0 N sodium bicarbonate (150 ml, then 50 ml). Acidify the aqueous layer to pH 1 with concentrated hydrochloric acid, extract twice with ether (150 ml, then 50 ml). Wash the organic layer with brine, dry over anhydrous magnesium sulfate and concentrate in vacuo to obtain crude 7-benzyloxycarbonyl-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid as an oil (16.1 g).

Workup

  1. additionPour the reaction mixture
  2. washWash the organic layer with water (3×175 ml)
  3. extractionthen extract twice with 1.0 N sodium bicarbonate (150 ml
  4. extractionextract twice with ether (150 ml
  5. washWash the organic layer with brine
  6. dry with materialdry over anhydrous magnesium sulfate
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f54a4c9de5774df8829e6e5233218138
Source dataset
uspto-grants-1984_09
Patent number
US04470972

Reaction notes

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