(1S,2R)-(-)-1-Amino-2-indanol → HCID 68493121, compound

HRID 1822439Notes

Reaction equation

HRID 1822439 reaction equation
C([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])C.C(OC(C1(NC(C2CC(OC3C4C(=CC(OC)=CC=4)N=C(C4C=CC=CC=4)C=3)CN2C(=O)NC([C:82](=[O:94])[NH:83][CH:84]2[C:92]3[C:87](=[CH:88][CH:89]=[CH:90][CH:91]=3)[CH2:86][CH:85]2[OH:93])C(C)(C)C)=O)CC1C=C)=O)C.C1C2C(=CC=CC=2)[C@H](N)[C@@H]1O.OC1CC2C(=CC=CC=2)C1NC(C(N1CC(OC2C3C(=CC(OC)=CC=3)C=C(C3C=CC=CC=3)C=2)CC1C1(C(O)=O)CC1C=C)C(C)(C)C)=O>>[OH:93][C@@H:85]1[CH2:86][C:87]2[C:92](=[CH:91][CH:90]=[CH:89][CH:88]=2)[C@@H:84]1[NH:83][C:82]([N:15]1[CH2:16][C@H:17]([O:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=3)[N:23]=[C:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:21]=2)[CH2:18][C@H:14]1[C:12]([NH:11][C@:6]1([C:4]([OH:3])=[O:5])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:13])=[O:94]

Participants

5

Reactant 4

HCID 9866743(1S,2R)-(-)-1-Amino-2-indanolHCID 207653161-{[4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 684916281-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 68493461HCID 68493461, compound

Product 1

HCID 68493121HCID 68493121, compound

Procedure

Compound 12 was treated as described for the preparation of 13 but with the use of (1S,2R)-cis-1-amino-2-indanol instead of 2-amino-N-(2-hydroxyindan-1-yl)-3,3-dimethyl butyramide followed by ester hydrolysis as described for the preparation of compound 14 which gave the title compound. Purity by HPLC>95%. M+H+649.1.

Sources & evidence

ORD record
ord-4de00a94e5174b4f908970141af1e47a
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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