Hydrochloric Acid → (2S,4S)-ethyl 2-amino-4-(benzyloxymethyl)-5-methylhexanoate

HRID 660381Notes

Reaction equation

HRID 660381 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([CH:27]([CH3:29])[CH3:28])[CH2:11][C@H:12]1[C:17]([O:18][CH2:19][CH3:20])=N[C@H](C(C)C)C(OCC)=[N:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=[O:32].[Na+]>CC#N>[NH2:13][C@@H:12]([CH2:11][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:27]([CH3:29])[CH3:28])[C:17]([O:18][CH2:19][CH3:20])=[O:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68784201(2S,5R)-2-((S)-2-(benzyloxymethyl)-3-methylbutyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine

Product 1

HCID 70642505(2S,4S)-ethyl 2-amino-4-(benzyloxymethyl)-5-methylhexanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S,5R)-2-((S)-2-(benzyloxymethyl)-3-methylbutyl)-3,6-diethoxy-5-isopropyl-2,5-dihydropyrazine (17.5 g, 46.8 mmol) in CH3CN (187 mL) was added 1 N aq HCl (187 mL, 187.2 mol) at rt and stirring was continued for 1.5 h. The mixture was poured into ice-cold, satd aq NaHCO3 and extracted with EtOAc (3×200 mL). The combined organic layers were washed with brine, dried and evaporated to afford (2S,4S)-ethyl 2-amino-4-(benzyloxymethyl)-5-methylhexanoate as a pale yellow oil (13.5 g) which was used in the next step without purification.

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-543069d197e24248bcb90b0bbd158c97
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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