Ethanol → HCID 72737722, compound

HRID 630599Notes

Reaction equation

HRID 630599 reaction equation
[C:1](Cl)(=[O:40])[O:2][C@@:3]([CH3:39])([C:6](=[O:38])[C@@H:7]([NH:15][C:16](=[O:37])[C@@H:17]([NH:21][C:22](=[O:36])[C@@H:23]([NH:27][C:28]([C:30]1[S:34][C:33]([CH3:35])=[N:32][CH:31]=1)=[O:29])[CH2:24][O:25][CH3:26])[CH2:18][O:19][CH3:20])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][I:5].[CH2:42]([OH:44])[CH3:43]>>[C:1](=[O:40])([O:2][C@@:3]([CH3:39])([C:6](=[O:38])[C@@H:7]([NH:15][C:16](=[O:37])[C@@H:17]([NH:21][C:22](=[O:36])[C@@H:23]([NH:27][C:28]([C:30]1[S:34][C:33]([CH3:35])=[N:32][CH:31]=1)=[O:29])[CH2:24][O:25][CH3:26])[CH2:18][O:19][CH3:20])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][I:5])[O:44][CH2:42][CH3:43]

Participants

3

Reactant 2

HCID 702EthanolHCID 86715355HCID 86715355, compound

Product 1

HCID 72737722HCID 72737722, compound

Procedure

Prepared according to procedures described above, by reacting ethanol with the intermediate (2S,4S)-1-iodo-4-((S)-3-methoxy-2-((S)-3-methoxy-2-(2-methylthiazole-5-carboxamido)propanamido)propanamido)-2-methyl-3-oxo-5-phenylpentan-2-yl carbonochloridate. 1H NMR (CDCl3): δ 8.05 (s, 1H), 7.28-7.16 (m, 5H), 7.08 (d, J=9.2 Hz, 1H), 6.96 (d, J=7.2 Hz, 1H), 6.84 (d, J=6 Hz, 1H), 5.44-5.40 (m, 1H). 4.71-4.66 (m, 1H), 4.48-4.44 (m, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.84-3.79 (m, 2H). 3.75-3.72 (m, 1H), 3.62 (d, J=11.2 Hz, 1H), 3.55 (t, J=4.8 Hz, 1H), 3.45 (s, 3H), 3.41-3.38 (m, 1H), 3.28 (s, 3H), 3.19-3.14 (m, 1H), 2.89-2.83 (m, 1H), 2.74 (s, 3H), 1.51 (s, 3H), 1.35 (t, J=7.2 Hz, 3H); MS for C28H37IN4O9S m/z: 733 (M+H)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1c038a723b4a4b8badfbed5274be71d4
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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