Boc-D-Homoserine lactone → HCID 66972798, compound

HRID 1367825Notes

Reaction equation

HRID 1367825 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9]([O:13][C:14](=[O:22])[NH:15][C@@H:16]1[CH2:20][CH2:19][O:18][C:17]1=[O:21])([CH3:12])([CH3:11])[CH3:10]>CO>[C:9]([O:13][C:14]([NH:15][C@@H:16]([CH2:20][CH2:19][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=1)[C:17]([OH:21])=[O:18])=[O:22])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 688319Boc-D-Homoserine lactoneHCID 5360545SodiumHCID 178418616HCID 178418616, compound

Product 1

HCID 66972798HCID 66972798, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Clean sodium metal (0.205 g, 8.95 mmol) was added, in portions, to anhydrous methanol (20 mL) in a thick walled tube. The suspension was stirred under anhydrous nitrogen until all the metal had dissolved, then pyridine-2-thiol (1.0 g, 8.95 mmol) was added. After stirring for 20 min, (2-oxotetrahydro-furan-3(R)-yl)-carbamic acid tert-butyl ester (1.8 g, 8.95 mmol) was added as a solid and the tube was capped and heated to 100° C. for 16 h. The reaction mixture was concentrated, then purified via flash chromatography (MeOH, CH2Cl2 as eluent) to give 2(S)-tert-butoxycarbonylamino-4-(pyridin-2-ylsulfanyl)butyric acid (0.75 g) as a clear oil.

Workup

  1. dissolutionhad dissolved
  2. stirringAfter stirring for 20 min
  3. customthe tube was capped
  4. concentrationThe reaction mixture was concentrated
  5. custompurified via flash chromatography (MeOH, CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-9ec84624319146c3bd66b713f13e2e66
Source dataset
uspto-grants-2011_02
Patent number
US07893093B2

Reaction notes

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