4-Methoxybenzenesulfonyl chloride → HCID 69780457, compound

HRID 1279035Notes

Reaction equation

HRID 1279035 reaction equation
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(=O)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:98])[CH2:81][C@H:82]([NH:86][S:87]([C:90]1[CH:95]=[CH:94][C:93]([O:96][CH3:97])=[CH:92][CH:91]=1)(=[O:89])=[O:88])[C:83](O)=[O:84])([CH3:78])[CH3:77].N[C@H](C(O)=O)CC(=O)OC(C)(C)C.COC1C=CC(S([Cl:123])(=O)=O)=CC=1>>[ClH:123].[CH3:78][C:76]([O:79][C:80](=[O:98])[CH2:81][C@H:82]([NH:86][S:87]([C:90]1[CH:91]=[CH:92][C:93]([O:96][CH3:97])=[CH:94][CH:95]=1)(=[O:89])=[O:88])[C:83]([NH:67][CH:58]([CH2:57][C:53]1[CH:52]=[C:51]2[C:56](=[CH:55][CH:54]=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:84])([CH3:75])[CH3:77]

Participants

6

Reactant 5

HCID 74014-Methoxybenzenesulfonyl 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 69781634HCID 69781634, compound

Product 1

HCID 69780457HCID 69780457, compound

Procedure

The procedure described for 5c was used. Deprotection of 100 mg of 5a and coupling with 99 mg of (2S)-[[(4-methoxyphenyl)sulfonyl]amino]butanedioic acid 4-(1,1-dimethylethyl)ester (prepared from Asp(OtBu)-OH and 4-methoxyphenylsulfonylchloride using the procedure described for 5b) yielded the title compound (85 mg) as a mixture of diastereomers (1:1). 1H-NMR 400 MHz (CD3OD) δ: 1.25-1.67 (6H, m), 1.32 and 1.35 (9H, 2× s), 2.18-2.48 (2H, m), 3.96-3.55 (6H, m), 3.83 and 3.86 (3H, 2× s), 4.04-4.14 (1H, m), 5.05-5.17 (1H, m), 6.99-7.05 (2H, m), 7.19-7.23 (1H, m), 7.51-7.79 (5H, m), 8.30-8.36 (1H, m).

Sources & evidence

ORD record
ord-22d1e88ca4dc4c64b8aaa919016b196d
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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