HCID 59997205, compound → HCID 56986106, compound

HRID 1815557Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:31][CH:30]=1)[C@H:3]([OH:27])[CH2:4][N:5]([CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][CH2:22][C:23]#[N:24])[S:6]([C:9]1[CH:17]=[CH:16][C:12]2[O:13][CH2:14][O:15][C:11]=2[CH:10]=1)(=[O:8])=[O:7].[O:43]1[CH2:47][CH2:46][C@H:45]([O:48][C:49](ON2C(=O)CCC2=O)=[O:50])[CH2:44]1.C(NC(C)C)(C)C.C(#N)C>>[O:13]1[C:12]2[CH:16]=[CH:17][C:9]([S:6]([N:5]([CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][CH2:22][C:23]#[N:24])[CH2:4][C@@H:3]([OH:27])[C@@H:2]([NH:1][C:49](=[O:50])[O:48][C@H:45]3[CH2:46][CH2:47][O:43][CH2:44]3)[CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[CH:33][CH:34]=3)(=[O:8])=[O:7])=[CH:10][C:11]=2[O:15][CH2:14]1

Participants

Reactant 2

HCID 59997205HCID 59997205, compound

HCID 86593030HCID 86593030, compound

Product 1

HCID 56986106HCID 56986106, compound

Procedure

N-{(2R,3S)-3-Amino-4-[4-(benzyloxy)phenyl]-2-hydroxybutyl}-N-(5-cyano-2,2-dimethylpentyl)-1,3-benzodioxole-5-sulfonamide was treated with 1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione/diisopropylamine/acetonitrile as previously described to provide the title product as a solid foam. 1H NMR (DMSO-d6): δ 0.88 (3H, s), 0.90 (3H, s), 1.3 (2H, dd), 1.5-1.6 (2H, m), 1.7-1.8 (1H, m), 2.0-2.2 (1H, m), 2.37 (1H, t), 2.4 (2H, t), 2.75-2.85 (3H, m), 2.9 (1H, dd), 3.30-3.45 (3H, m), 3.55 (1H, dd), 3.65 (1H, dd), 3.7 (2H, dd), 4.9 (1H, s), 4.98 (1H, d), 5.0 (2H, s), 6.15 (2H, s), 6.8 (2H, d), 7.0 (2H, d), 7.06 (2H, d), 7.24 (1H, s), 7.25-7.42 (6H, m); MS: 708 (MH+);

Sources & evidence

ORD record: ord-ac2fef967dee4bf4b5181af3c4ec2df3
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878728B1

Reaction notes

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