Water → (2R,5RS)-2-Amino-5-{2-[4-(2-fluoro-ethoxy)-phenyl]-ethyl}-hexanedioic acid

HRID 591316Notes

Reaction equation

HRID 591316 reaction equation
C([O:5][C:6](=[O:38])[C@@H:7]([NH:30]C(OC(C)(C)C)=O)[CH2:8][CH2:9][CH:10]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][F:29])=[CH:22][CH:21]=1)[C:11]([O:13]C(C)(C)C)=[O:12])(C)(C)C.FC(F)(F)C(O)=O.O.C(#N)C>ClCCl>[NH2:30][C@H:7]([CH2:8][CH2:9][CH:10]([CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][F:29])=[CH:24][CH:25]=1)[C:11]([OH:13])=[O:12])[C:6]([OH:38])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 89156295(2S)-2-tert.-Butoxycarbonylamino-5-{2-[4-(2-fluoro-ethoxy)-phenyl]-ethyl}-hexanedioic acid di-tert.-butyl ester

Product 1

HCID 89156264(2R,5RS)-2-Amino-5-{2-[4-(2-fluoro-ethoxy)-phenyl]-ethyl}-hexanedioic acidYield 16.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 mg (37 μmol) of (2S)-2-tert.-Butoxycarbonylamino-5-{2-[4-(2-fluoro-ethoxy)-phenyl]-ethyl}-hexanedioic acid di-tert.-butyl ester were dissolved in 2 mL dichloromethane (dried over 4{acute over (Å)} molecular sieve) and 1 mL trifluoroacetic acid were added. The reaction was stirred at room temperature for 30 min, after which the solution was directly applied to reversed phase chromatography on a Biotage system (Flash 12+M cartridge, A=water, B=acetonitrile, A 1 CV, A to 50% B in 10 CV, 2 CV 50% B, 12 mL/min). Fraction 6 was lyophilized to give 2 mg (11%) of (2R,5RS)-2-Amino-5-{2-[4-(2-fluoro-ethoxy)-phenyl]-ethyl}-hexanedioic acid as the Tfa-salt.

Sources & evidence

ORD record
ord-8d687aa6190a43fbb5b9c0cf18f1e257
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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