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Hydrochloric Acid → N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-{[6-N-(4-methoxybenzyloxycarbonyl)-adenin-9-yl]-acetyl}-glycine ethyl ester

HRID 1246345
Notes
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Reaction equation

HRID 1246345 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[CH3:2].[CH3:23][O:24][C:25]1[CH:48]=[CH:47][C:28]([CH2:29][O:30][C:31]([NH:33][C:34]2[N:42]=[CH:41][N:40]=[C:39]3[C:35]=2[N:36]=[CH:37][N:38]3[CH2:43][C:44](O)=[O:45])=[O:32])=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[C:44](=[O:45])[CH2:43][N:38]1[CH:37]=[N:36][C:35]2[C:39]1=[N:40][CH:41]=[N:42][C:34]=2[NH:33][C:31]([O:30][CH2:29][C:28]1[CH:47]=[CH:48][C:25]([O:24][CH3:23])=[CH:26][CH:27]=1)=[O:32])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21868398HCID 21868398, compoundHCID 21868443Ethyl 2-((2-(benzo[d]thiazole-2-sulfonamido)ethyl)amino)acetate

Product 1

HCID 21868450
N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-{[6-N-(4-methoxybenzyloxycarbonyl)-adenin-9-yl]-acetyl}-glycine ethyl ester
Yield 102.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (172 mg, 0.5 mmol), [6-N-(4-methoxybenzyloxycarbonyl)-adenin-9-yl]-acetic acid (179 mg, 0.5 mmol), and HBTU (190 mg, 0.5 mmol) in DMF (2 ml) was added diisopropylethylamine (0.09 ml, 0.5 mmol) at ambient temperature. The resulting reaction mixture was stirred for 2 h at the same temperature and 1N HCl was added to the reaction mixture. The resulting precipitate product was filtered off, washed with water, and dried in vacuo to give the title compound as a white solid (0.35 g, 97%). 1H NMR (500 MHz; DMSO-d6) δ 8.97 (t, 0.6H) 8.76 (t, 0.4H) 8.64 (s, 0.4H) 8.60 (s, 0.6H) 8.53 (d, 1H) 8.28 (m, 1H) 8.17 (d, 1H) 7.66 (m, 2H) 7.40 (d, 2H) 6.95 (d, 2H) 5.41 (s, 1.2H), 5.20 (s, 0.8H) 5.18 (s, 2H) 4.46 (s, 0.8H) 4.18 (q, 0.8H) 4.08 (s, 1.2H) 4.03 (q, 1.2H) 3.75 (s, 3H) 3.70 (q, 1.2H) 3.48 (q, 1.2H) 3.42 (t, 0.8H) 3.22 (q, 0.8H) 1.24 (t, 1.2H) 1.13 (t, 1.8H)

Workup

  1. customThe resulting reaction mixture
  2. additionwas added to the reaction mixture
  3. filtrationThe resulting precipitate product was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c0c9f8ca78f940c588f79a6e2f2f1ef2
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07125994B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes