Hydrochloric Acid → HCID 11236684, compound

HRID 1270990Notes

Reaction equation

HRID 1270990 reaction equation
C(O[C:6](=[O:33])[C@@H:7]([NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.C(OC(=O)[C@@H]([NH2:48])CC1C=CC=CC=1)(C)(C)C.C1(O[C:57](=O)[NH:58][C:59]2[CH:64]=CC(OC3C=CC(Cl)=CC=3)=CC=2)C=CC=CC=1.Cl>CS(C)=O.CCOC(C)=O>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([O:25][C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:16](=[O:17])[NH:15][C@@H:7]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([NH:48][CH2:64][CH2:59][NH:58][CH3:57])=[O:33])=[CH:24][CH:23]=2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 69430366HCID 69430366, compoundHCID 69435159HCID 69435159, compound

Product 1

HCID 11236684HCID 11236684, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-{3-[4-(4-Chloro-phenoxy)-phenyl]-ureido}-3-phenyl-propionic acid tert-butyl ester. To a stirred solution of (S)-2-amino-3-phenyl-propionic acid tert-butyl ester (0.2 g, 0.9 mmol) in DMSO (2 mL) was added [4-(4-chloro-phenoxy)-phenyl]-carbamic acid phenyl ester (0.3 g, 0.9 mmol). The mixture was stirred at rt overnight. EtOAc (80 mL) was then added, along with 0.1 N HCl (5 mL). The organic layer was washed sequentially with H2O (10 mL), 1 N NaOH (10 mL) and brine (20 mL), and dried (MgSO4). The solvent was removed. Purification by column chromatography [0–20% of (1% NH4OH/MeOH)/CH2Cl2] afforded 0.35 g (83%) of the desired product. MS (electrospray): mass calculated for C26H27ClN2O4, 466.17; m/z found, 411.1 [M−tBu+H]+. 1H NMR (400 MHz, CDCl3): 7.22–7.13 (m, 5H), 7.10–7.07 (m, 4H), 6.82–6.78 (m, 4H), 6.70 (s, 1H), 4.66 (s, 1H), 3.03 (dd, J=13.9, 6.06 Hz, 1H), 2.94 (dd, J=13.8, 6.07 Hz, 1H), 1.37 (s, 9H).

Workup

  1. washThe organic layer was washed sequentially with H2O (10 mL), 1 N NaOH (10 mL) and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed
  4. customPurification by column chromatography [0–20% of (1% NH4OH/MeOH)/CH2Cl2]

Sources & evidence

ORD record
ord-c3402a616f4045deade9d18e8ed91665
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

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