Benzyl Alcohol → HCID 68181333, compound

HRID 535196Notes

Reaction equation

HRID 535196 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:17]C(OC(C)(C)C)=O)[CH2:9][C@:10]([CH2:15][OH:16])([CH3:14])[C:11](O)=[O:12])=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:52]([OH:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.CN1CCOCC1.CC#N.Cl>C(Cl)Cl.O1CCOCC1>[CH2:52]([O:59][C:11](=[O:12])[C@@:10]([CH2:15][OH:16])([CH3:14])[CH2:9][C@H:8]([NH2:17])[CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:2][CH:3]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

10

Reactant 7

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68181022(2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid

Product 1

HCID 68181333HCID 68181333, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

(2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (100 mg, 242 μmol), HOBt (98 mg, 726 μmol), and EDCI (128 μL, 726 μmol) were dissolved in DCM (2 mL). After stirring for 15 minutes, benzyl alcohol (200 μL, 1.9 mmol) and 4-methylmorpholine (106 μL, 967 μmol) were added. The resulting mixture was stirred at room temperature overnight, and then the reaction was quenched with water. The DCM layer was separated, concentrated, purified ((Interchim reverse phase chromatography column), and dried under vacuum. The purified material was combined with MeCN (1 mL, 20 mmol) and 4 M HCl in dioxane (240 μL, 970 μmmol) and stirred at room temperature for 1 hour. The solvent was then removed to yield (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyl ester.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customthe reaction was quenched with water
  3. customThe DCM layer was separated
  4. concentrationconcentrated
  5. custompurified ((Interchim reverse phase chromatography column)
  6. customdried under vacuum
  7. stirringstirred at room temperature for 1 hour
  8. customThe solvent was then removed

Sources & evidence

ORD record
ord-d66cf4755d1b4b2fa0125f305955546d
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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