3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-oxobutyric Acid → 3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(6-chloro-4-fluorobenzoxazol-2-yl)-4-oxobutyric Acid

HRID 1456658Notes

Reaction equation

HRID 1456658 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]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:14][C:15]([NH:17][C@H](C(C1OC=C(C2C(Cl)=CC=CC=2Cl)N=1)=O)CC(O)=O)=[O:16])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C(N)[C@H](C(OCC=C)=O)C(C1OC=C(C2C(Cl)=CC=CC=2Cl)N=1)O)(C)(C)C.C([O:83][C:84](=[O:107])[CH:85](N)[C@H:86](C(OCC=C)=O)[CH:87]([C:89]1[O:90][C:91]2[CH:97]=[C:96]([Cl:98])[CH:95]=[C:94]([F:99])[C:92]=2[N:93]=1)[OH:88])(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]([CH3:47])[CH3:46])[C:11]([N:13]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:14][C:15]([NH:17][C@H:86]([C:87]([C:89]1[O:90][C:91]2[CH:97]=[C:96]([Cl:98])[CH:95]=[C:94]([F:99])[C:92]=2[N:93]=1)=[O:88])[CH2:85][C:84]([OH:83])=[O:107])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 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 697241953(S)-(Allyloxycarbonyl)-amino-4-((2,6-dichloro-phenyl)oxazol-2-yl)-4-hydroxy-butyric Acid tert-Butyl EsterHCID 697258443(S)-(Allyloxycarbonyl)-amino-4-(6-chloro-4-fluorobenzoxazol-2-yl)-4-hydroxy-butyric Acid tert-Butyl Ester

Product 1

HCID 540578373(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(6-chloro-4-fluorobenzoxazol-2-yl)-4-oxobutyric Acid

Procedure

Compound 719 was prepared by a method similar to the method used to prepare compound 710, except compound 707 was replaced with compound 714 in the preparation of 708: 1H NMR (500 MHz, CD3OD) δ 8.70-8.54 (m), 8.48-8.35 (m), 8.34-8.08 (m), 7.98-7.87 (m), 7 .75-7.67 (m), 7.63 (m), 7.58 (m), 7.51-7.44 (m), 7.43-7.29 (m), 7.28-7.03 (m), 6.97 (m), 5.51 (m), 4.99-4.66 (m), 4.65-4.26 (m), 4.25-3.61 (m), 3.42 (m), 3.13-2.83 (m), 2.68-2.42 (m), 2.23-2.00 (m), 1.02-0.69 (m). ##STR98##

Sources & evidence

ORD record
ord-403b93931307449bb9246918135f16fd
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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