N-Acetyl-L-phenylalanine → HCID 67139620, compound

HRID 1591989Notes

Reaction equation

HRID 1591989 reaction equation
C1C=CC2N(O)N=NC=2C=1.[C:11]([NH:14][C@@H:15]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16](O)=[O:17])(=[O:13])[CH3:12].CCN=C=NCCCN(C)C.Cl.[NH2:38][C@@H:39]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH2:55][N:56]2[CH2:60][C:59](=[O:61])[N:58]([CH2:62][C:63]3[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[CH:65][CH:64]=3)[S:57]2(=[O:72])=[O:71])[CH:50]=1)[C:40]([NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:41]>C(Cl)Cl>[C:11]([NH:14][C@@H:15]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:16]([NH:38][C@@H:39]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH2:55][N:56]2[CH2:60][C:59](=[O:61])[N:58]([CH2:62][C:63]3[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[CH:65][CH:64]=3)[S:57]2(=[O:71])=[O:72])[CH:50]=1)[C:40]([NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:41])=[O:17])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 74839N-Acetyl-L-phenylalanineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67138311HCID 67138311, compound

Product 1

HCID 67139620HCID 67139620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBt (19 mg, 0.125 mmol), (S)-2-acetylamino-3-phenyl-propionic acid (26 mg, 0.125 mmol) and EDCl (26 mg, 0.138 mmol) are added to a solution of the title G compound, (S)-2-amino-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-phenyl}-N-pentylpropionamide (63 mg, 0.125 mmol) in CH2Cl2 (4 mL) at RT. After 30 min, the reaction is concentrated. The product is taken up in EtOAc, washed with 1N aqueous HCl, saturated aqueous NaHCO3 and brine. The organic solution is dried over anhydrous MgSO4 and concentrated to yield (S)-2-((S)-2-acetylamino-3-phenyl-propionylamino)-3-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-phenyl}-N-pentyl-propionamide as a white foam: [M+1]+=692.

Workup

  1. concentrationthe reaction is concentrated
  2. washwashed with 1N aqueous HCl, saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic solution is dried over anhydrous MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9edac9711f7646c7b43bee1ed81085a4
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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