3-Pyridinecarboxaldehyde → 3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)-3-picolylamino)acetyl-amino)-4-(4,6-dichlorobenzoxazol-2-yl)-4-oxobutyric Acid

HRID 1456659Notes

Reaction equation

HRID 1456659 reaction equation
[C:1]([NH:9][C@@H:10]([CH:45]([CH3:47])[CH3:46])[C:11]([N:13]([CH2:38][C:39]1[CH:44]=C[CH:42]=[CH:41][CH:40]=1)[CH2:14][C:15]([NH:17][C@H:18]([C:23]([C:25]1[O:26]C=C(C2C(Cl)=CC=CC=2Cl)[N:29]=1)=[O:24])[CH2:19][C:20]([OH:22])=[O:21])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:48]1C=CC=C(C=O)C=1.C(OC(=O)CNCC1C=CC=CC=1)C.C(OC(=O)C(N)[C@H](C(OCC=C)=O)C(C1O[C:82]2[CH:88]=[C:87]([Cl:89])[CH:86]=[C:85]([Cl:90])[C:83]=2N=1)O)(C)(C)C.C(OC(=O)C[C@H](NC(=O)CN(C(=O)[C@@H](NC(=O)C1C=CC=CC=1)C(C)C)CC1C=CC=CC=1)C(C1OC=C(C2C(Cl)=CC=CC=2Cl)N=1)O)(C)(C)C>>[C:1]([NH:9][C@@H:10]([CH:45]([CH3:46])[CH3:47])[C:11]([N:13]([CH2:38][C:39]1[CH:44]=[N:48][CH:42]=[CH:41][CH:40]=1)[CH2:14][C:15]([NH:17][C@H:18]([C:23]([C:25]1[O:26][C:82]2[CH:88]=[C:87]([Cl:89])[CH:86]=[C:85]([Cl:90])[C:83]=2[N:29]=1)=[O:24])[CH2:19][C:20]([OH:22])=[O:21])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 103713-PyridinecarboxaldehydeHCID 80908N-Benzylglycine ethyl esterHCID 536861393(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-oxobutyric AcidHCID 544408483(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-hydroxybutyric Acid tert-Butyl EsterHCID 1317209653(S)-(Allyloxycarbonyl)-amino-4-(4,6-dichorobenzoxazol-2-yl)-4-hydroxy-butyric Acid tert-Butyl Ester

Product 1

HCID 538074383(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)-3-picolylamino)acetyl-amino)-4-(4,6-dichlorobenzoxazol-2-yl)-4-oxobutyric Acid

Procedure

Compound 720 was prepared by a method similar to the method used to prepare compound 710, except replacing benzaldehyde with 3-pyridinecarboxaldehyde in the preparation of 701 and replacing compound 707 with compound 718 in the preparation of 708: 1H NMR (500 MHz, CD3OD) δ 8.88-8.44 (m), 8.42-8.20 (m), 7.91-7.58 (m), 7.55-7.30 (m), 5.51 (m), 4.72-4.11 (m), 3.92-3.52 (m), 3.26-2.92 (m), 2.72-2.51 (m), 2.32-1.91 (m), 1.46-1.21 (m), 1.11-0.68 (m). ##STR99##

Sources & evidence

ORD record
ord-bd0f59eb14ab4325bf6f6d696307418d
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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