Hydrochloric Acid → (4S)-4-[4-(2-fluoroethoxy)-3-hydroxybenzyl]-L-glutamic acid

HRID 591328Notes

Reaction equation

HRID 591328 reaction equation
Cl.C(OC([NH:9][C@H:10]([C:36]([O:38]C(C)(C)C)=[O:37])[CH2:11][C@H:12]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][F:30])=[C:23]([O:31]C(C)(C)C)[CH:22]=1)[C:13]([O:15]C(C)(C)C)=[O:14])=O)(C)(C)C>O1CCOCC1>[F:30][CH2:29][CH2:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][C@@H:10]([C:36]([OH:38])=[O:37])[NH2:9])=[CH:22][C:23]=1[OH:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117812704di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-[3-tert-butoxy-4-(2-fluoroethoxy)benzyl]-L-glutamate

Product 1

HCID 89155775(4S)-4-[4-(2-fluoroethoxy)-3-hydroxybenzyl]-L-glutamic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrogen chloride in dioxane (0.25 ml, 4M) is added to 24 mg (0.041 mmol) di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-[3-tert-butoxy-4-(2-fluoroethoxy)benzyl]-L-glutamate. The reaction mixture is stirred for 4 hours and stored at −25° C. over night. The reaction mixture is concentrated in vacuo. Co. 3 ml dichloro methane is added and the solution is concentrate in vacuo. The last step is repeated. The crude product is purified by HPLC (column, XBrigde, C18, 5 μm 100×30 mm, H2O+0.1% trifluoroacetic acid, acetonitrile, flow 38 mL/min).

Workup

  1. waitstored at −25° C. over night
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. addition3 ml dichloro methane is added
  4. concentrationthe solution is concentrate in vacuo
  5. customThe crude product is purified by HPLC (column, XBrigde, C18, 5 μm 100×30 mm, H2O+0.1% trifluoroacetic acid, acetonitrile, flow 38 mL/min)

Sources & evidence

ORD record
ord-ae9e3cdc69a64614ab44fa54cb8678d7
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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