Methanesulfonic Acid → HCID 66851381, compound

HRID 876353Notes

Reaction equation

HRID 876353 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][CH:12]1[C:17]([C:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[BH4-].CS(O)(=O)=O>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][CH:12]1[CH2:17][C:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 4148881Lithium borohydrideHCID 66809409HCID 66809409, compound

Product 1

HCID 66851381HCID 66851381, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
11 °C

Procedure

To a suspension of 6 (10.1 g, 26 mmol) in anhydrous THF (200 mL) was added 2M LiBH4 in THF (26.2 mL, 52 mmol) over ca. 7 min [Note: exothermic; temp. increase: 21.5° C. to 28.2° C.]. After 2.5 h, the pale, yellow-colored solution was cooled to ca. 11° C. and methanesulfonic acid (4.66 g, 48 mmol) was added over ca. 4 min [Note: exothermic; temp. increase to 14.2° C.].

Workup

  1. temperature[Note: exothermic; temp. increase: 21.5° C. to 28.2° C.]
  2. temperature[Note: exothermic; temp. increase to 14.2° C.]

Sources & evidence

ORD record
ord-78d9afc02bef4324a10c276fb94c7da6
Source dataset
uspto-grants-2015_03
Patent number
US08986993B2

Reaction notes

Loading…