Triethylamine → Methyl 1-benzenesulfonyl-7-chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(tert-butoxycarbonylmethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate

HRID 1439910Notes

Reaction equation

HRID 1439910 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[C:12]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]1([S:32]([N:35]2[C:43]3[CH:42]=[C:41]([Cl:44])[CH:40]=[C:39]4[CH2:45][CH2:46][CH:47]([CH2:48][C:49](O)=[O:50])[C:37]([C:38]=34)=[C:36]2[C:52]([O:54][CH3:55])=[O:53])(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:26]1([S:32]([N:35]2[C:43]3[CH:42]=[C:41]([Cl:44])[CH:40]=[C:39]4[CH2:45][CH2:46][CH:47]([CH2:48][C:49](=[O:50])[NH:14][C:13]5[CH:15]=[CH:16][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:11][C:12]=5[O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:37]([C:38]=34)=[C:36]2[C:52]([O:54][CH3:55])=[O:53])(=[O:34])=[O:33])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15337219Methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylateHCID 196983594-tert-Butoxycarbonylaminomethyl-2-tert-butoxycarbonylmethoxyaniline

Product 1

HCID 18984723Methyl 1-benzenesulfonyl-7-chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(tert-butoxycarbonylmethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylateYield 103.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-tert-butoxycarbonylaminomethyl-2-tert-butoxycarbonylmethoxyaniline (202 mg, 0.574 mmol), methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (250 mg, 0.574 mmol), triethylamine (0.2 mL, 1.43 mmol), and N,N-bis(2-oxo-3-oxazolidinyl)-phosphinic chloride (Bop-Cl, 161 mg, 0.631 mmol) in dichloromethane (5 mL) was stirred for 15 h at room temperature and diluted with ethyl acetate. The mixture was washed successively with 5% potassium hydrogen sulfate, water, saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, and concentrated to give 463 mg of the title compound (quant): 1H NMR (CDCl3) δ8.63 (s, 1H), 8.33 (d, 1H, J=8.6 Hz), 8.03 (d, 2H, J=6.9 Hz), 7.92 (s, 1H), 7.58 (t, 1H, J=6.9 Hz); 7.52 (t, 2H, J=6.9 Hz), 7.06 (s, 1H), 6.94 (d, 1H, J=Hz), 6.80 (s, 1H), 4.82 (br, 1H), 4.35 (s, 2H), 4.12 (d, 2H, J=7.3 Hz), 3.89 (s, 3H), 3.86 (m, 1H), 3.03 (mt, 1H, J=14.7 Hz), 2.81 (m, 1H), 2.81 (dd, 1H, J=14.7, 4.3 Hz), 2.53 (dd, 1H, J=14.7, 10.4 Hz), 2.22 (m, 1H), 1.72 (m, 1H), 1.46 (s, 9H), 1.45 (s, 9H).

Workup

  1. washThe mixture was washed successively with 5% potassium hydrogen sulfate, water, saturated sodium bicarbonate, water, and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-14f4450a5791413e9b46290ae4178c9f
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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