N-Acetyl-L-phenylalanine → HCID 67139939, compound

HRID 1592049Notes

Reaction equation

HRID 1592049 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][C:52]([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:51][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:50]=[CH:51][C:52]([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:53][CH:54]=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 67138785HCID 67138785, compound

Product 1

HCID 67139939HCID 67139939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBt (16 mg, 0.102 mmol), (S)-2-acetylamino-3-phenyl-propionic acid (21 mg, 0.102 mmol) and EDCl (21 mg, 0.112 mmol) are added to a solution of the title B compound, (S)-2-amino-3-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-N-pentyl-propionamide (50 mg, 0.102 mmol) in CH2Cl2 (3 mL) and the reaction is stirred at RT for 2.5 h, then concentrated. The residue is taken up in EtOAc, washed with 1N aqueous HCl, saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated to yield (S)-2-acetylamino-N-((S)-2-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-1-pentylcarbamoyl-ethyl)-3-phenyl-propionamide as a white foam: [M+1]+=678.

Workup

  1. concentrationconcentrated
  2. washwashed with 1N aqueous HCl, saturated NaHCO3 and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-08294fcfec8444d28ec098b146ec396c
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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