3-(4-Chlorobenzoyl)propionic acid → 2-(Carboxymethoxy)-5-[(2S)-2-{[(3R)-3-carboxy-4-phenylbutanoyl]amino}-3-oxo-3-(pentylamino)propyl]benzoic Acid

HRID 2188462

Reaction equation

HRID 2188462 reaction equation
C(O[C:9](=[O:38])[C@@H:10]([NH:30][C:31]([O:33]C(C)(C)C)=O)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:23][CH2:24][C:25]([O:27]CC)=[O:26])=[C:16]([CH:22]=1)[C:17]([O:19]CC)=[O:18])C1C=CC=CC=1.I[C:40]1[CH:41]=[C:42]([CH:49]=[CH:50][C:51]=1O)[CH2:43][C@@H:44]([C:46]([OH:48])=[O:47])N.[NH2:53][C@H:54](C(OCC1C=CC=CC=1)=O)[CH2:55][C:56]1C=CC(OCC(OCC)=O)=[C:60]([CH:66]=1)C(OCC)=O.Cl[C:85]1C=CC(C(CCC(O)=O)=O)=CC=1.C(OC(=O)[C@@H](NC(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)CC1C=CC(OCC(OCC)=O)=C(C=1)C(OCC)=O)C1C=CC=CC=1>>[C:25]([CH2:24][O:23][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][C@H:10]([NH:30][C:31](=[O:33])[CH2:85][C@H:44]([C:46]([OH:48])=[O:47])[CH2:43][C:42]2[CH:49]=[CH:50][CH:51]=[CH:40][CH:41]=2)[C:9](=[O:38])[NH:53][CH2:54][CH2:55][CH2:56][CH2:66][CH3:60])=[CH:22][C:16]=1[C:17]([OH:19])=[O:18])([OH:27])=[O:26]

Participants

6

Reactant 5

HCID 776043-(4-Chlorobenzoyl)propionic acidHCID 4397443-Iodo-L-TyrosineHCID 57257659Ethyl 5-[(2S)-2-Amino-3-(benzyloxy)-3-oxopropyl]-2-(2-ethoxy-2-oxoethoxy)benzoate4×HCID 70160131Ethyl 5-{(2S)-3-(Benzyloxy)-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}-2-(2-ethoxy-2-oxoethoxy)benzoate2×HCID 70160837Ethyl 5-((2S)-3-(Benzyloxy)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-oxopropyl)-2-(2-ethoxy-2-oxoethoxy)benzoate

Product 1

HCID 701609422-(Carboxymethoxy)-5-[(2S)-2-{[(3R)-3-carboxy-4-phenylbutanoyl]amino}-3-oxo-3-(pentylamino)propyl]benzoic Acid

Procedure

The title compound was prepared in analogy with the preparation of the compound of Example 151 above. MS (FAB) m/z (rel. intensity) 543 (MH+, 25), 544 (9), 543 (25), 309 (15), 263 (9), 233 (10), 231 (48), 154 (99), 137 (58), 109 (15), 91 (16). MS (FAB) m/z (rel. intensity) 543 (MH+, 99), 565 (20), 544 (33), 543 (99), 238 (25), 117 (16), 107 (16), 88 (58), 43 (23), 41 (16), 23 (17). HRMS (FAB) calcd for C28H34N2O9+H1 543.2343, found 543.2353. Anal. Calcd for C28H34N2O9: C, 61.98; H, 6.32; N, 5.16. Found: C, 60.35; H, 6.35; N, 4.89.

Sources & evidence

ORD record
ord-0849198a13874ac2825be787f584b42e
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Linked notes

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