Thionyl Chloride → (S)-4-Amino-5-biphenyl-4-yl-pentanoic acid ethyl ester hydrochloride

HRID 1021053Notes

Reaction equation

HRID 1021053 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C@H:7]([NH:21]C(OC(C)(C)C)=O)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH3:2].S(Cl)([Cl:32])=O>C(O)C>[ClH:32].[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C@H:7]([NH2:21])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53829475(S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylaminopentanoic acid ethyl ester

Product 1

HCID 66738936(S)-4-Amino-5-biphenyl-4-yl-pentanoic acid ethyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylaminopentanoic acid ethyl ester [9-a, R1=Boc, R2=H, R5=Et] (115 g) in ethanol (1.1 L) at 70° C. is added thionyl chloride (32 ml) over 45 min. After a further 1.5 hours, the mixture is concentrated to dryness. The crude material is suspended in ethyl acetate and filtered to give (S)-4-Amino-5-biphenyl-4-yl-pentanoic acid ethyl ester hydrochloride [10-a, R5=Et]. 1H NMR (DMSO): 1.08 (3H, d, CH3); 1.73 (2H, m, 3-CH2); 2.35-2.52 (2H, m, 2-CH2); 2.79 (1H, dd, 5-CHH); 2.97 (1H, dd, CHH); 3.38 (1H, m, 4-CH); 3.97 (2H, q, CH2CH3); 7.30 (3H, m, aromatic); 7.40 (2H, m, aromatic); 7.58 (4H, m, aromatic); 8.15 (3H, s, NH3+). m/z: 298 (MH+, 100%); 281 (4); 235 (3).

Workup

  1. concentrationthe mixture is concentrated to dryness
  2. filtrationfiltered

Sources & evidence

ORD record
ord-38ca8e3416b7402390532c70012320d5
Source dataset
uspto-grants-2014_05
Patent number
US08716495B2

Reaction notes

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