(R)-3-amino-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one → 3-(Benzyloxycarbonylamino)-2,2-dimethyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-propanamide

HRID 1591465Notes

Reaction equation

HRID 1591465 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C@@H:20]1[CH2:26][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[NH:22][C:21]1=[O:31]>>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([CH3:18])([CH3:17])[C:14]([NH:19][C@@H:20]1[CH2:26][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[NH:22][C:21]1=[O:31])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10103689(R)-3-amino-4,5-dihydro-1H-benzo[b]azepin-2(3H)-oneHCID 145510103-(((Benzyloxy)carbonyl)amino)-2,2-dimethylpropanoic acid

Product 1

HCID 186514583-(Benzyloxycarbonylamino)-2,2-dimethyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-propanamide

Procedure

Prepared from 3-(benzyloxycarbonylamino)-2,2-dimethylpropanoic acid and 3(R)-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (Example 1, Step B) by the procedure described in Example 1, Step F. 1H NMR (200 MHz, CDCl3): 1.19 (s,6H), 1.90 (m,1H), 2.6-3.0 (m,3H), 3.26 (d,6 Hz,2H), 4.46 (m,1H), 5.07 (s,2H), 5.7 (br t,1H), 6.62 (d,7 Hz,1H), 6.97 (d,8 Hz,1H), 7.1-7.3 (m,3H), 7.3 (s,5H), 8.14 (br s,1H). FAB-MS: calculated for C23H27N3O4 409; found 410 (M+H,100%).

Sources & evidence

ORD record
ord-c2a9291e477b4638ac7d025fca47b47f
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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