Methyl chloroformate → HCID 86708780, compound

HRID 1751576Notes

Reaction equation

[NH2:1][C@@H:2]([CH:52]1[CH2:57][CH2:56][S:55][CH2:54][CH2:53]1)[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[CH:27]=[C:26]([C:31]3[NH:35][C:34]([C@@H:36]5[CH2:40][CH2:39][CH2:38][N:37]5[C:41](=[O:51])[C@@H:42]([NH:46][C:47](=[O:50])[O:48][CH3:49])[CH:43]([CH3:45])[CH3:44])=[N:33][CH:32]=3)[CH:25]=[CH:24]4)=[CH:17][CH:16]=2)=[CH:13][N:14]=1)=[O:4].C([O-])([O-])=O.[Na+].[Na+].Cl[C:65]([O:67][CH3:68])=[O:66]>O>[CH3:68][O:67][C:65](=[O:66])[NH:1][C@@H:2]([CH:52]1[CH2:53][CH2:54][S:55][CH2:56][CH2:57]1)[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([C:31]5[NH:35][C:34]([C@@H:36]6[CH2:40][CH2:39][CH2:38][N:37]6[C:41](=[O:51])[C@@H:42]([NH:46][C:47]([O:48][CH3:49])=[O:50])[CH:43]([CH3:44])[CH3:45])=[N:33][CH:32]=5)[CH:27]=4)[CH:22]=3)=[CH:17][CH:16]=2)=[CH:13][N:14]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To methyl (S)-1-((S)-2-(5-(6-(4-(2-((S)-1-((S)-2-amino-2-(tetrahydro-2H-thiopyran-4-yl)acetyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (30 mg, 0.06 mmol) in water (0.3 mL) was add Na2CO3 (13 L, 0.09 mmol). The reaction mixture was cooled to 0° C. and methyl chloroformate (0.12 mmol) was added and then stirred for 2 hours. The resulting mixture was then directly purified on reverse phase prep. HPLC to afford title compound as white solid (20 mg, 65%). MS (ESI) m/z 848 [M+H]+.

Workup

customThe resulting mixture was then directly purified on reverse phase prep

Sources & evidence

ORD record: ord-d9c484045a484adbb4f8a7c721389be1
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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