Methanol → HCID 11120630, compound

HRID 1911542Notes

Reaction equation

HRID 1911542 reaction equation
[BH4-].[Li+].C[O:4][C:5](=O)[C@@H:6]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9].CO.C(OC(C)(C)C)=O>O1CCCC1>[C:21]([O:20][C:18](=[O:19])[NH:17][C@H:6]([CH2:5][OH:4])[CH2:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 61207tert-Butyl FormateHCID 4148881Lithium borohydrideHCID 68715991HCID 68715991, compound

Product 1

HCID 11120630HCID 11120630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium borohydride in tetrahydrofuran (2M, 1.14 ml, 2.28 mmol) was added slowly at 0° C. a solution of (R)-3-benzenesulfonyl-2-tert-butoxycarbonylamino-propionic acid methyl ester (0.52 g, 1.51 mmol) in tetrahydrofuran (3 ml). After stirring at room temperature for 2.5 hours methanol was added (0.5 ml). The mixture was partitioned between ethyl acetate and saturated ammoniumchloride solution. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (SiO2, heptane/EtOAc=1:1 to yield a white solid, (0.292 g, 61%); MS (ISP): 316.0 ((M+H)+/); 216.1 ((M+H—BOC)+.).

Workup

  1. additionwas added (0.5 ml)
  2. customThe mixture was partitioned between ethyl acetate and saturated ammoniumchloride solution
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (SiO2, heptane/EtOAc=1:1
  7. customto yield a white solid, (0.292 g, 61%)

Sources & evidence

ORD record
ord-eea36d475f404851be4e34bc0dfe0080
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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