N-Acetyl-L-phenylalanine → HCID 67139666, compound

HRID 1592060Notes

Reaction equation

HRID 1592060 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]([N:55]2[CH2:59][C:58](=[O:60])[N:57]([CH2:61][C:62]3[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=3)[S:56]2(=[O:71])=[O:70])[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]([C:40](=[O:41])[NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([N:55]2[CH2:59][C:58](=[O:60])[N:57]([CH2:61][C:62]3[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=3)[S:56]2(=[O:70])=[O:71])[CH:50]=1)=[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 67138347HCID 67138347, compound

Product 1

HCID 67139666HCID 67139666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBt (40.5 mg, 0.264 mmol), (S)-2-acetylamino-3-phenyl-propionic acid (54.7 mg, 0.264 mmol) and EDCl (50.6 mg, 0.264 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-yl]-phenyl}-N-pentyl-propionamide (129 mg, 0.264 mmol) in CH2Cl2 (5 mL) and stirred at RT for 2 h. The reaction is concentrated and the product is taken up in EtOAc, washed with 1N aqueous HCl, saturated aqueous NaHCO3 and brine, dried over magnesium sulfate, filtered and concentrated to yield (S)-2-acetylamino-N-((S)-2-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-1-pentylcarbamoyl-ethyl)-3-phenyl-propionamide as a white solid: [M+1]+=678.

Workup

  1. concentrationThe reaction is concentrated
  2. washwashed with 1N aqueous HCl, saturated aqueous NaHCO3 and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b1dd5ffeb4644168b4091e129e936e9f
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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