Hydrochloric Acid → Methyl O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serinate Hydrochloride

HRID 1265221Notes

Reaction equation

HRID 1265221 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[NH:8][C@H:9]([C:31]([O:33][CH3:34])=[O:32])[CH2:10][O:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]([NH:27][CH2:28][CH2:29][CH3:30])=[O:26])[CH:19]=3)[CH:15]=[CH:16][CH:17]=2)C=CC=CC=1.[ClH:47]>CO.C(OCC)C>[ClH:47].[CH2:28]([NH:27][C:25]([NH:24][C:20]1[CH:19]=[C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C@@H:9]([C:31]([O:33][CH3:34])=[O:32])[NH2:8])[CH:13]=2)[CH:23]=[CH:22][CH:21]=1)=[O:26])[CH2:29][CH3:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11215663Methyl N-triphenylmethyl-O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serinate

Product 1

HCID 69940921Methyl O-(3'-{[(propylamino)carbonyl]amino}-1,1'-biphenyl-3-yl)-L-serinate Hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Methyl N-triphenylmethyl-O-(3′-{[(propylamino)carbonyl]amino}-1,1′-biphenyl-3-yl)-L-serinate (Example 4) (291.2 mg, 0.48 mmol, 1 equiv) was dissolved in MeOH and treated with a 1 M solution of HCl in diethylether at rt. The solution was stirred for 2 h at rt and then the solvents were removed in vacuuo. The crude product was titurated with ether to give a yellow precipitate which was filtered off and dried in vacuo. Yield 195.0 mg, 99%. 1H NMR (DMSO, 200 MHz) δ 8.85 (brs, 2H); 7.82 (s, 1H); 7.55 (d, 2H); 7.49-7.22 (m, 3H); 7.05 (d, 2H); 4.85-4.55 (m, 1H); 4.49-4.29 (m, 2H); 3.80 (s, 3H); 2.92 (dd, 1H); 1.60-1.29 (m, 3H); 0.96 (t, 3H).

Workup

  1. customthe solvents were removed in vacuuo
  2. customto give a yellow precipitate which
  3. filtrationwas filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a7c1982794774597a8d22f5a42f4e73d
Source dataset
uspto-grants-2003_04
Patent number
US06545029B2

Reaction notes

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