HCID 86727349, compound → HCID 90220745, compound

HRID 519044Notes

Reaction equation

HRID 519044 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[CH:27]([CH3:29])[CH3:28])[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:31])[C:18](=[O:30])[NH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CC(OC2C=C3C(=CC=2Br)OCC2N3C(C)C(=O)NN=2)C1)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[CH:27]([CH3:28])[CH3:29])[O:23][CH2:22][C:21]2[N:16]3[C@@H:17]([CH3:31])[C:18](=[O:30])[NH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[CH:27]([CH3:28])[CH3:29])[O:23][CH2:22][C:21]2[N:16]3[C@H:17]([CH3:31])[C:18](=[O:30])[NH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 86727349HCID 86727349, compoundHCID 86727353HCID 86727353, compound

Product 2

HCID 86727411HCID 86727411, compoundYield 47%HCID 90220745HCID 90220745, compoundYield 50%

Procedure

Racemic 3-(7-isopropyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (prepared from the corresponding bromide (Example #65, Step G) with similar procedure as descried in Example #57, Step A-B, 0.090 g, 0.210 mmol) was separated by chiral SFC (Table 2, Method 7) to give 3-(7-isopropyl-4(S)-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (Enantiomer 1, SFC (Table 1, Method 13) Rt=1.572 min.; 0.045 g, 50%) and 3-(7-isopropyl-4(R)-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (Enantiomer 2, SFC (Table 1, Method 13) Rt=2.104 min, 0.042 g, 47%).

Workup

  1. customwas separated by chiral SFC (Table 2, Method 7)

Sources & evidence

ORD record
ord-2d99be04262b4817aeb3cd0047950506
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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