(R)-2-Amino-1-(3-chlorophenyl)ethanol → diethyl (2S)-2-[[5-[[4-[4-[[(2R)-2-hydroxy-2-[4-hydroxy-3-(methanesulfonamido)phenyl]ethyl]amino]piperidin-1-yl]phenyl]methylidene]-4-oxo-1,3-thiazol-2-yl]amino]pentanedioate

HRID 2188301Notes

Reaction equation

HRID 2188301 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[C@@H:5]([NH:13][C:14]1[S:15][C:16](=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:36][CH2:35][C:30]4(OCCO4)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[C:17](=[O:19])[N:18]=1)[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].[NH2:38][CH2:39][C@@H:40]([C:42]1[CH:43]=[CH:44][C:45]([OH:53])=[C:46]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])[CH:47]=1)[OH:41].CNC1SC(=CC2C=CC(N3CCC(=O)CC3)=CC=2)C(=O)N=1.NC[C@@H](C1C=CC=C(Cl)C=1)O>>[CH2:1]([O:3][C:4](=[O:37])[C@@H:5]([NH:13][C:14]1[S:15][C:16](=[CH:20][C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH2:28][CH2:29][CH:30]([NH:38][CH2:39][C@H:40]([OH:41])[C:42]4[CH:43]=[CH:44][C:45]([OH:53])=[C:46]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])[CH:47]=4)[CH2:35][CH2:36]3)=[CH:25][CH:26]=2)[C:17](=[O:19])[N:18]=1)[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2]

Participants

5

Reactant 4

HCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanolHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide2×HCID 178471552diethyl (2S)-2-[[5-[[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]methylidene]-4-oxo-1,3-thiazol-2-yl]amino]pentanedioate2×HCID 1784824352-(methylamino)-5-[[4-(4-oxopiperidin-1-yl)phenyl]methylidene]-1,3-thiazol-4-one

Product 1

HCID 178471553diethyl (2S)-2-[[5-[[4-[4-[[(2R)-2-hydroxy-2-[4-hydroxy-3-(methanesulfonamido)phenyl]ethyl]amino]piperidin-1-yl]phenyl]methylidene]-4-oxo-1,3-thiazol-2-yl]amino]pentanedioate

Procedure

The title compound was prepared from (2S)-2-{5-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzylidene]-4-oxo-4,5-dihydro-thiazol-2-ylamino}-pentanedioic acid diethyl ester (which was obtained in Intermediate 34) and N-[5-(2-amino-(1R)-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Intermediate 10) according to the procedures of Intermediate 18 and Example 1 as a yellowish solid; mp>130° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ1.19(t, J=7.0 Hz, 3 H), 1.22(t, J=7.0 Hz, 3 H), 1.70-3.00 (m,14 H), 2.92(s, 3 H), 3.50-3.90 (m, 2 H), 4.05(q, J=7.0 Hz, 2 H), 4.14(q, J=7.0 Hz, 2 H), 4.48(dd, J=8.0, 4.3 Hz, 1 H), 4.68(dd, J=8.7, 5.4 Hz, 1 H), 6.82(d, J=8.2 Hz, 1 H), 7.02(dd, J=8.2, 2.0 Hz, 1 H), 7.05(d, J=8.9 Hz, 2 H), 7.18(d, J=2.0 Hz, 1 H), 7.40(d, J=8.9 Hz, 2 H), 7.50 (s, 1 H), MS (ES) m/z: 359.5 ((M+2H)2+, 100%); 718.2 (MH+, 20%); HRMS Calcd. for C33H44N6O9S2 (MH+): 718.2575. Found: 718.2581.

Sources & evidence

ORD record
ord-ffea2206380144d48972dfea37335273
Source dataset
uspto-grants-2002_06
Patent number
US06410734B1

Reaction notes

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