1,2-Dichloroethane → HCID 59402226, compound

HRID 384607Notes

Reaction equation

HRID 384607 reaction equation
N[C@@H:2]([CH2:20][C:21]1C=CC=CC=1)[C:3](NCCC1C=C(Cl)C=CC=1N1C=NN=N1)=[O:4].[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([N:37]2[CH:41]=[N:40][N:39]=[N:38]2)=[C:32]([CH2:34][CH2:35][NH2:36])[CH:33]=1.C(O[C:47]([NH:49][C@@H:50]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:51]([OH:53])=O)=[O:48])(C)(C)C.C(Cl)CCl.C1C=CC2N([OH:74])N=NC=2C=1.CCN([CH:81]([CH3:83])[CH3:82])C(C)C>CN(C=O)C>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([N:37]2[CH:41]=[N:40][N:39]=[N:38]2)=[C:32]([CH:33]=1)[CH2:34][CH2:35][NH:36][C:51](=[O:53])[C@@H:50]([NH:49][C:47]([C:82]1[CH:81]=[CH:83][C:2]([C:3]([OH:74])=[O:4])=[CH:20][CH:21]=1)=[O:48])[CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81531DiisopropylethylamineHCID 59401998HCID 59401998, compoundHCID 68471486HCID 68471486, compound

Product 1

HCID 59402226HCID 59402226, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-amino-N-(5-chloro-2-(1H-tetrazol-1-yl)phenethyl)-3-phenylpropanamide: To a mixture of 2-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)ethanamine (0.179 g, 0.8 mmol), (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (0.233 g, 0.880 mmol), EDC (0.169 g, 0.880 mmol) and HOBt (0.135 g, 0.880 mmol) in DMF (10 mL) was added DIEA (excess, 1.0 mL). The resulted mixture was stirred at rt for 2.5 h. Most of the solvent was removed and the residue was diluted with ethyl acetate, washed with water, 1N HCl, sat. NaHCO3, brine and dried over anhydrous MgSO4 to obtain the desired product as a white solid. LCMS m/z 471.4.

Workup

  1. customMost of the solvent was removed
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water, 1N HCl, sat. NaHCO3, brine
  4. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-f5bcedd3fead4dc691b7e57bcfb6e6c7
Source dataset
uspto-grants-2013_02
Patent number
US08367709B2

Reaction notes

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