6-Oxoheptanoic acid → Nalpha-Acetyl-p-(6-Oxo-n-Heptanoylamino)-L-Phenylalanyl-Glycine Benzyl Ester

HRID 280045

Reaction equation

HRID 280045 reaction equation
C(OC(=O)CNC(=O)[C@H](CC1C=CC([N+]([O-])=O)=CC=1)NC(OC(C)(C)C)=O)C1C=CC=CC=1.[O:34]=[C:35]([CH3:43])[CH2:36][CH2:37][CH2:38][CH2:39][C:40]([OH:42])=O.[CH2:44]([O:51][C:52](=[O:70])[CH2:53][NH:54][C:55](=[O:69])[C@H:56]([CH2:61][C:62]1[CH:67]=[CH:66][C:65]([NH2:68])=[CH:64][CH:63]=1)[NH:57][C:58](=[O:60])[CH3:59])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CO>[CH2:44]([O:51][C:52](=[O:70])[CH2:53][NH:54][C:55](=[O:69])[C@H:56]([CH2:61][C:62]1[CH:67]=[CH:66][C:65]([NH:68][C:40](=[O:42])[CH2:39][CH2:38][CH2:37][CH2:36][C:35](=[O:34])[CH3:43])=[CH:64][CH:63]=1)[NH:57][C:58](=[O:60])[CH3:59])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 988106-Oxoheptanoic acidHCID 13934182Nalpha-t-Butyloxycarbonyl-p-Nitro-L-Phenylalanyl-Glycine Benzyl EsterHCID 54160731Nalpha-Acetyl-p-Amino-L-Phenylalanyl-Glycine Benzyl Ester

Product 1

HCID 53767188Nalpha-Acetyl-p-(6-Oxo-n-Heptanoylamino)-L-Phenylalanyl-Glycine Benzyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixed anhydride coupling was performed as described for the synthesis of compound 13 with 6-oxo-n-heptanoic acid (97 mg, 0.67 mmol) and the product from above, compound 15 (238 mg, 0.67 mmol). Each component was dissolved in 10 ml of dry tetrahydrofaran. Yield 111 mg (34%), mp 177.5°-180.5° C., [α]D25 =+19.5 (c.=1.4, methanol). Anal. calc. for C27H33N3O6 (493.58): C, 65.44; H, 6.71; N, 8.48. Found: C, 65.46; H, 6.74; N, 8.61.

Workup

  1. dissolutionEach component was dissolved in 10 ml of dry tetrahydrofaran

Sources & evidence

ORD record
ord-27bd1b361a22467289ac874c4e5e9004
Source dataset
uspto-grants-1986_05
Patent number
US04587046

Linked notes

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