4-Methylmorpholine → HCID 10046415, compound

HRID 2248492Notes

Reaction equation

HRID 2248492 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:47]([O:54][C:55](=[O:59])[CH2:56][CH2:57][NH2:58])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1COCC1>[CH2:47]([O:54][C:55](=[O:59])[CH2:56][CH2:57][NH:58][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:10]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 8541623-(((Tert-butoxy)carbonyl)amino)benzoic acidHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)

Product 1

HCID 10046415HCID 10046415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For the preparation of the ester starting material, m-(1-t-butoxyformamido)benzoic acid in THF is activated (2 hours, 0° C.) with 2-chloro-4,6-dimethoxy-1,3,5-triazine and N-methylmorpholine and reacted with β-alanine benzyl ester p-toluenesulphonate and N-methylmorpholine to give N-[m-(1-t-butoxyformamido)benzoyl]-β-alanine benzyl ester, m.p. 130°-131° C. Cleavage with trifluoroacetic acid gives N-(m-aminobenzoyl)-β-alanine benzyl ester trifluoroacetate. Nα -Z-Nω -Nitro-L-arginine is activated (4 minutes, -10° C.) with isobutyl chloroformate and triethylamine in THF and coupled with N-(m-aminobenzoyl)-β-alanine benzyl ester trifluoroacetate and triethylamine to give the desired benzyl ester, m.p. 157°-160° C.

Workup

  1. custom(2 hours, 0° C.)

Sources & evidence

ORD record
ord-4a20be4981e146f2885d8c652a64051d
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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