Spiro(1-benzopyran-2,4'-piperidin)-4(3H)-one--hydrogen chloride (1/1) → N-[1(R)-[(3,4-dihydro-4-oxospiro[2H-1-benzopyran-2,4'-piperidin]1'-yl)carbonyl]-2-(indol-3-yl)ethyl]-2-[[(1,1-dimethylethyloxy)carbonyl]amino]-2-methylpropanamide

HRID 266894Notes

Reaction equation

HRID 266894 reaction equation
[CH3:1][C:2]([CH3:28])([O:4][C:5]([NH:7][C:8]([CH3:27])([CH3:26])[C:9]([NH:11][C@H:12]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:13]([OH:15])=O)=[O:10])=[O:6])[CH3:3].Cl.[NH:30]1[CH2:35][CH2:34][C:33]2([CH2:40][C:39](=[O:41])[C:38]3[CH:42]=[CH:43][CH:44]=[CH:45][C:37]=3[O:36]2)[CH2:32][CH2:31]1>>[O:41]=[C:39]1[C:38]2[CH:42]=[CH:43][CH:44]=[CH:45][C:37]=2[O:36][C:33]2([CH2:34][CH2:35][N:30]([C:13]([C@H:12]([NH:11][C:9](=[O:10])[C:8]([NH:7][C:5]([O:4][C:2]([CH3:28])([CH3:1])[CH3:3])=[O:6])([CH3:27])[CH3:26])[CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)=[O:15])[CH2:31][CH2:32]2)[CH2:40]1

Participants

3

Reactant 2

HCID 2771097Spiro(1-benzopyran-2,4'-piperidin)-4(3H)-one--hydrogen chloride (1/1)HCID 15895387(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acid

Product 1

HCID 22875166N-[1(R)-[(3,4-dihydro-4-oxospiro[2H-1-benzopyran-2,4'-piperidin]1'-yl)carbonyl]-2-(indol-3-yl)ethyl]-2-[[(1,1-dimethylethyloxy)carbonyl]amino]-2-methylpropanamide

Procedure

This intermediate was prepared from α(R)-[[2-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-1-oxoethyl]amino]-1H-indole-3-propanoic acid (903 mg, 2.3 mmol) and spiro[2H-1-benzopyran-2,4'-piperidin]-4(3H)-one, hydrochloride (535 mg, 2.11 mmol) (Elliott, J., et al, J. Med. Chem. 1992, 35, 3973-3976) by the procedure described in Example 25, Step A (1.25 g, 100%).

Sources & evidence

ORD record
ord-7820cf1408444f56b32812c04ce3a855
Source dataset
uspto-grants-1997_07
Patent number
US05652235

Reaction notes

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