4-Methoxy-2,3,6-trimethylbenzenesulfonyl chloride → (3S)-4-[[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]amino]-3-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]4-oxo-butanoic acid 1,1-dimethylethylester hydrochloride

HRID 1008488

反応式

HRID 1008488 の反応式
Cl.NC1C2C(=CC(CC(NC(=O)CNS(C3C(C)=C(C)C4OC(C)(C)CCC=4C=3C)(=O)=O)C(=O)N3CCCCC3)=CC=2)C=CN=1.[NH2:46][C:47]1[C:56]2[C:51](=[CH:52][C:53]([CH2:57][CH:58]([NH:67][C:68](=[O:74])OC(C)(C)C)[C:59](=[O:66])[N:60]3[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:54][CH:55]=2)[CH:50]=[CH:49][N:48]=1.[CH3:75][C:76]([O:79][C:80](=[O:101])[CH2:81][C@H:82]([NH:86][S:87]([C:90]1[C:95]([CH3:96])=[CH:94][C:93]([O:97][CH3:98])=[C:92]([CH3:99])[C:91]=1[CH3:100])(=[O:89])=[O:88])C(O)=O)([CH3:78])[CH3:77].N[C@H](C(O)=O)CC(=O)OC(C)(C)C.COC1C=C(C)C(S([Cl:127])(=O)=O)=C(C)C=1C>>[ClH:127].[CH3:78][C:76]([O:79][C:80](=[O:101])[CH2:81][C@H:82]([NH:86][S:87]([C:90]1[C:95]([CH3:96])=[CH:94][C:93]([O:97][CH3:98])=[C:92]([CH3:99])[C:91]=1[CH3:100])(=[O:89])=[O:88])[C:68]([NH:67][CH:58]([CH2:57][C:53]1[CH:54]=[C:55]2[C:56](=[CH:51][CH:52]=1)[C:47]([NH2:46])=[N:48][CH:49]=[CH:50]2)[C:59](=[O:66])[N:60]1[CH2:61][CH2:62][CH2:63][CH2:64][CH2:65]1)=[O:74])([CH3:75])[CH3:77]

参加物

6

反応物 5

HCID 5627874-Methoxy-2,3,6-trimethylbenzenesulfonyl chlorideHCID 70105704-tert-Butyl hydrogen L-aspartateHCID 226656071,1-Dimethylethyl 1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl-carbamateHCID 22665631N-[1-[(1-Amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]-2-[[(3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-yl)sulfonyl]amino]acetamide hydrochlorideHCID 86588684(2S)-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]butanedioic acid 4-(1,1-dimethylethyl)ester

生成物 1

HCID 9831693(3S)-4-[[1-[(1-amino-6-isoquinolinyl)methyl]-2-oxo-2-(1-piperidinyl)ethyl]amino]-3-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]4-oxo-butanoic acid 1,1-dimethylethylester hydrochloride

実験手順

The procedure described for 5c was used. Deprotection of 5a and coupling with 121 mg of (2S)-2-[[(4-methoxy-2,3,6-trimethylphenyl)sulfonyl]amino]butanedioic acid 4-(1,1-dimethyl-ethyl)ester (prepared from Asp(OtBu)—OH and (4-methoxy-2,3,6-trimethylphenyl)-sulfonylchloride using the procedure described for 5b) yielded after purification 8 as a mixture of diastereomers (1:1). 1H-NMR 200 MHz (CD3OD) δ: 1.30 and 1.35 (9H, 2× s), 1.38-1.70 (6H, m), 2.12 and 2.14 (3H, 2× s) 2.18-2.51 (2H, m), 2.53 and 2.54, (3H, 2× s), 2.63 (3H, s) 2.85-3.54 (6H, m), 3.81 and 3.86 (3H, 2× s), 3.95-4.11 (1H, m), 5.03-5.21 (1H, 6.73 and 6.75 (1H, 2× s), 7.17-7.24 (1H, m), 7.52-7.78 (3H, m), 8.30-8.38 (1H, m).

後処理

  1. customyielded
  2. customafter purification 8
  3. additionas a mixture of diastereomers (1:1)

出典と根拠

ORDレコード
ord-32841f3c50954aa9b3b6e6db3ebb8603
出典データセット
uspto-grants-2004_09
特許番号
US06797710B2

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