1,2-Dichloroethane → N-[1(R)-[(3,4-dihydro-6-methyl-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 266892Notes

Reaction equation

HRID 266892 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]2[O:16][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH2:9][C:8](=[O:17])[C:7]=2[CH:18]=1.[CH3:19][C:20]([CH3:46])([O:22][C:23]([NH:25][C:26]([CH3:45])([CH3:44])[C:27]([NH:29][C@H:30]([CH2:34][C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[NH:37][CH:36]=1)[C:31](O)=[O:32])=[O:28])=[O:24])[CH3:21].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]2[O:16][C:10]3([CH2:11][CH2:12][N:13]([C:31]([C@H:30]([NH:29][C:27](=[O:28])[C:26]([NH:25][C:23]([O:22][C:20]([CH3:46])([CH3:21])[CH3:19])=[O:24])([CH3:45])[CH3:44])[CH2:34][C:35]4[C:43]5[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=5)[NH:37][CH:36]=4)=[O:32])[CH2:14][CH2:15]3)[CH2:9][C:8](=[O:17])[C:7]=2[CH:18]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 15895387(R)-2-(2-((tert-Butoxycarbonyl)amino)-2-methylpropanamido)-3-(1H-indol-3-yl)propanoic acidHCID 190304256-Methylspiro[chroman-2,4'-piperidin]-4-one hydrochloride

Product 1

HCID 22862457N-[1(R)-[(3,4-dihydro-6-methyl-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

Prepared by the procedure described in Example 3, Step B. 3,4-Dihydro-6-methylspiro[2H-1-benzopyran-2,4'-piperidine]-4-one hydrochloride (20 mg, 0.058 mmol), (Hashigaki et al Chem. Pharm. Bull. 32 pg 3561-3568 (1984)) α(R)-[[2-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-1-oxoethyl]amino]-1H-indole-3-propanoic acid) (32 mg, 0.082 mmol), HOBT (1 eq.), N-methyl morpholine (0.03 mL, 0.28 mmol), and EDC (40 mg, 0.21 mmol). Reaction time: 8 hours. Yield: 34 mg (86%).

Workup

  1. customPrepared by the procedure
  2. customReaction time
  3. custom8 hours

Sources & evidence

ORD record
ord-4d61161777c747e2a8f0c2bf04b116f7
Source dataset
uspto-grants-1997_07
Patent number
US05652235

Reaction notes

Loading…