tert-Butyl (piperazin-1-yl)acetate → HCID 53864541, compound

HRID 1415676Notes

Reaction equation

HRID 1415676 reaction equation
C(N1CCN(CC(NC2C=C(C=CC=2)C(NCCC(O)=O)=O)=O)CC1)(=N)N.[C:28]([N:38]1[CH2:43][CH2:42][N:41]([CH:44]([C:69](=[NH:71])[NH2:70])[C:45](NC2C=C(C=CC=2)C(NCCC(OCC2C=CC=CC=2)=O)=O)=[O:46])[CH2:40][CH2:39]1)([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].N1(CC([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=O)CCNCC1.C(NC(=N)SC)(OCC1C=CC=CC=1)=O>>[C:28]([N:38]1[CH2:39][CH2:40][N:41]([CH:44]([C:69](=[NH:71])[NH2:70])[C:45]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:46])[CH2:42][CH2:43]1)([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29]

Participants

5

Reactant 4

HCID 2757326tert-Butyl (piperazin-1-yl)acetateHCID 9821029HCID 9821029, compoundHCID 53812397HCID 53812397, compoundHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

Product 1

HCID 53864541HCID 53864541, compound

Procedure

3-(3-(4-amidinopiperazin-1-ylacetamido)benzamido)propionic acid, m.p. 270° (decomposition), from benzyl 3-(3-(4-CBZ-amidinopiperazin-1-ylacetamido)benzamido)propionate (FAB 601; obtainable by reacting tert-butyl piperazin-1-ylacetate with N-CBZ-S-methylisothiourea to give tert-butyl 4-CBZ-amidinopiperazin-1-ylacetate, cleaving the tert-butyl group with 4 N HCl in dioxane and condensing the resulting 4-CBZ-amidinopiperazin-1-ylacetic acid with benzyl 3-(3-aminobenzamido)propionate);

Sources & evidence

ORD record
ord-90bdff9b7c8a4264b06d3c5f7ba2c8b9
Source dataset
uspto-grants-1999_06
Patent number
US05908843

Reaction notes

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