Methanol → HCID 86757202, compound

HRID 1386913Notes

Reaction equation

CO.C(Cl)(=O)C.[CH3:7][C:8]([O:11][C:12]([C@@H:14]1[CH2:30][S:29][S:28][CH2:27][C@H:26]([NH:31]C(OC(C)(C)C)=O)[C:25](=[O:39])[NH:24][CH2:23][CH2:22][C:17]2([CH2:21][CH2:20][CH2:19][CH2:18]2)[C:16](=[O:40])[NH:15]1)=[O:13])([CH3:10])[CH3:9]>C(OCC)(=O)C>[CH3:10][C:8]([O:11][C:12]([C@@H:14]1[CH2:30][S:29][S:28][CH2:27][C@H:26]([NH2:31])[C:25](=[O:39])[NH:24][CH2:23][CH2:22][C:17]2([CH2:18][CH2:19][CH2:20][CH2:21]2)[C:16](=[O:40])[NH:15]1)=[O:13])([CH3:7])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of methanol (0.15 mL, 3.8 mmol) in 5 mL of ethyl acetate was added at 0° C., under an atmosphere of argon, acetyl chloride (0.27 mL, 3.8 mmol). The solution was stirred at 0° C. for 10 min, and at room temperature for 30 min. To the solution was added (8R,13R)-13-[[(1,1-dimethylethoxy)carbonyl]amino]-6,14-dioxo-10,11-dithia-7,15-diazaspiro[4.12]heptadecane-8-carboxylic acid 1,1-dimethylethyl ester (130 mg, 0.25 mmol). The mixture was stirred for 7 hours. The precipitate was collected on a glass frit and washed with ethyl ether. After drying under high vacuum, 92 mg of (8R,13R)-13-amino-6,14-dioxo-10,11-dithia-7,15-diazaspiro[4.12]heptadecane-8-carboxylic acid 1,1-dimethylethyl ester was obtained (96% yield based on recovered starting material after evaporation of the filtrate and washes).

Workup

additionwas added at 0° C., under an atmosphere of argon
waitat room temperature for 30 min
stirringThe mixture was stirred for 7 hours
customThe precipitate was collected on a glass frit
washwashed with ethyl ether
customAfter drying under high vacuum

Sources & evidence

ORD record: ord-d8f9ab67dbe442238386e47d93ab334e
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265572B1

Reaction notes

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