(2S)-2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoyl)amino]-3-(4-tert-butoxyphenyl)propanoic acid → N-(5-{[3-(4-[(carboxycarbonyl)(2-carboxyphenyl)amino]-1-naphthyl)-N-(methoxycarbonyl)alanyl]amino}pentanoyl)-L-methionine

HRID 488650Notes

Reaction equation

C(NC(CC1C=CC(N(C(=O)C(OC(C)(C)C)=O)C2C=CC=CC=2C(OC(C2C=CC=CC=2)C2C=CC=CC=2)=O)=C(CC)C=1)C(NCCCCC(N[C@@H](CC1C=CC(OC(C)(C)C)=CC=1)C(O)=O)=O)=O)(=O)C.C([O:86][C:87]([C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][C:90]=1[N:95]([C:132](=[O:140])[C:133]([O:135]C(C)(C)C)=[O:134])[C:96]1[C:105]2[C:100](=[CH:101][CH:102]=[CH:103][CH:104]=2)[C:99]([CH2:106][C@@H:107]([C:113]([NH:115][CH2:116][CH2:117][CH2:118][CH2:119][C:120]([NH:122][C@H:123]([C:128]([O:130]C)=[O:129])[CH2:124][CH2:125][S:126][CH3:127])=[O:121])=[O:114])[NH:108][C:109]([O:111][CH3:112])=[O:110])=[CH:98][CH:97]=1)=[O:88])(C1C=CC=CC=1)C1C=CC=CC=1>>[C:133]([C:132]([N:95]([C:90]1[CH:91]=[CH:92][CH:93]=[CH:94][C:89]=1[C:87]([OH:88])=[O:86])[C:96]1[C:105]2[C:100](=[CH:101][CH:102]=[CH:103][CH:104]=2)[C:99]([CH2:106][C@@H:107]([C:113]([NH:115][CH2:116][CH2:117][CH2:118][CH2:119][C:120]([NH:122][C@H:123]([C:128]([OH:130])=[O:129])[CH2:124][CH2:125][S:126][CH3:127])=[O:121])=[O:114])[NH:108][C:109]([O:111][CH3:112])=[O:110])=[CH:98][CH:97]=1)=[O:140])([OH:135])=[O:134]

Participants

Reactant 2

HCID 86585322(2S)-2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoyl)amino]-3-(4-tert-butoxyphenyl)propanoic acid

HCID 87999852methyl N-(5-{[3-(4-{{2-[(benzhydryloxy)carbonyl]phenyl}[tert-butoxy(oxo)acetyl]amino}-1-naphthyl)-N-(methoxycarbonyl)alanyl]amino}pentanoyl)-L-methioninate

Product 1

HCID 10146804N-(5-{[3-(4-[(carboxycarbonyl)(2-carboxyphenyl)amino]-1-naphthyl)-N-(methoxycarbonyl)alanyl]amino}pentanoyl)-L-methionine

Procedure

The titled compound was prepared according to the procedure described in Example 1L, substituting the ester from Example 1K with the ester from Example 7L. MS (ESI+) m/e 711 (M+H)+, 1H NMR (300 MHz, DMSO-d6) 1.23-1.64 (m, 4H), 1.71-2.22 (m, 4H), 2.03 (s, 3H), 2.35-2.56 (m, 2H), 2.97-3.59 (m, 7H), 4.00-4.67 (m, 2H), 6.70-7.80 (m, 6H), 7.86 (d, J=6.3 Hz, 1H), 7.92-8.34 (m, 4H), 8.43 (d, J=9.3 Hz, 1H).

Sources & evidence

ORD record: ord-da3cb4523b0f46718e0528c8a669766a
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972340B2

Reaction notes

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