Dimethyl Sulfide → Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-8-hydroxydecanoate

HRID 251728Notes

Reaction equation

HRID 251728 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C)[CH3:23]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([OH:21])[CH2:19][CH3:20])[C:10]([O:12][CH3:23])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 11197378HCID 11197378, compound

Product 1

HCID 86627956Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-8-hydroxydecanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-8-oxodecanoic acid in anhydrous THF at 0° C. under a nitrogen atmosphere was added slowly a solution of BH3.Me2S in THF (2 M, 2 eq.). The mixture was stirred for 5 min at 0° C. and 3 hr at 55° C. The reaction was quenched with MeOH and partitioned between EtOAc and sat. aq. NaHCO3. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The obtained product was used in the next step without purification. MS (ES) C16H31NO5 requires: 317, found: 318 (M+H)+.

Workup

  1. customThe reaction was quenched with MeOH
  2. custompartitioned between EtOAc and sat. aq. NaHCO3
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained product was used in the next step without purification

Sources & evidence

ORD record
ord-eb6f13cb7c644a33ae40f1b13faf9f14
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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