HCID 11213235, compound → HCID 11212313, compound

HRID 606639Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:33])[C:11]([CH2:31][NH2:32])=[C:12]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:13]([C:14]3[CH:19]=[CH:18]C=CC=3)=[C:8]2[S:7][CH2:6]1)=[O:4].COC([C@H]1N2C(=O)C(C#N)=C(CC3C4C(=CC=CC=4)C=CC=3)C(C3C=CC=CC=3)=C2SC1)=O.COC(C1N2C(=O)C(C#N)=C(CC3C4C(=CC=CC=4)C=CC=3)C(C3CC3)=C2SC1)=O>>[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:33])[C:11]([CH2:31][NH2:32])=[C:12]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:13]([CH:14]3[CH2:18][CH2:19]3)=[C:8]2[S:7][CH2:6]1)=[O:4]

Participants

Reactant 3

HCID 11213235HCID 11213235, compound

HCID 11339937HCID 11339937, compound

HCID 67048053HCID 67048053, compound

Product 1

HCID 11212313HCID 11212313, compoundYield 73%

Procedure

By following the procedure described for the preparation of 7a from 6a, 6b (46 mg, 0.11 mmol) gave 7b as a yellow solid (33 mg, 73%): [α]D−64 (c 0.25, CHCl3); IR X 2952, 1747, 1631, 1569, 1504, 1259, 1214 cm−1; 1H NMR (400 MHz, CDCl3) δ8.18 (d, J=8.2, 1H), 7.94-7.27 (m, 5H), 6.81 (d, J=6.8, 1H), 5.67 (d, J=7.3, 1H), 4.77-4.56 (m, 2H), 3.96-3.31 (m, 9H), 1.40 (m, 1H), 0.76-0.31 (m, 4H); 13C NMR (100 MHz, CDCl3) δ168.3, 161.1, 155.6149.5, 133.7, 133.7, 131.6, 128.7, 127.3, 126.4, 126.0, 125.5, 123.8, 123.4, 116.9, 115.7, 63.4, 53.5, 37.6, 32.6, 31.6, 11.8, 7.2, 7.1; HRMS (FAB+) calcd for C24H25N2O3S 421.1586, obsd 421.1593.

Sources & evidence

ORD record: ord-9b841deb220b4d748dae394d6e598a58
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915417B2

Reaction notes

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