Hydrochloric Acid → (E)-(S)-5-Amino-2-(3-fluoropropyl)hex-2-enedioic acid

HRID 1473721Notes

Reaction equation

HRID 1473721 reaction equation
C(OC([NH:8][C@H:9]([C:22]([O:24]C(C)(C)C)=[O:23])[CH2:10]/[CH:11]=[C:12](\[CH2:18][CH2:19][CH2:20][F:21])/[C:13]([O:15]CC)=[O:14])=O)(C)(C)C.Cl>O>[NH2:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10]/[CH:11]=[C:12](\[CH2:18][CH2:19][CH2:20][F:21])/[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866784276-tert-Butyl 1-ethyl (E)-(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoropropyl)hex-2-enedioate

Product 1

HCID 86678435(E)-(S)-5-Amino-2-(3-fluoropropyl)hex-2-enedioic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-tert-Butyl 1-ethyl (E)-(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoropropyl)hex-2-enedioate (1e) (80.0 mg, 0.20 mmol) and 4 N aqueous hydrochloric acid (1 mL) was heated to reflux for 4 h. The mixture was then cooled to r.t., diluted with water (5 mL) and lyophilised. The crude product was purified by preparative HPLC (XBridge C18, 5 μm 150×19 mm, acetonitrile/water (0.1% TFA) gradient, 21 mL/min). Yield: 12.0 mg, 0.04 mmol, 19%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe crude product was purified by preparative HPLC (XBridge C18, 5 μm 150×19 mm, acetonitrile/water (0.1% TFA) gradient, 21 mL/min)

Sources & evidence

ORD record
ord-d786353c42d54b028e90030b8695df1b
Source dataset
uspto-grants-2015_04
Patent number
US09017645B2

Reaction notes

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