Ammonia → HCID 58092782, compound

HRID 1807660Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]([CH2:8][C@@:9]12[CH2:21][CH2:20][CH2:19][N:10]1[C@@H](C(Cl)(Cl)Cl)[O:12][C:13]2=O)[CH3:7].[NH3:25].CO>>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]([CH2:8][C@@:9]1([C:13]([NH2:25])=[O:12])[CH2:21][CH2:20][CH2:19][NH:10]1)[CH3:7]

Participants

Reactant 3

HCID 222Ammonia

HCID 887Methanol

HCID 58092774HCID 58092774, compound

Product 1

HCID 58092782HCID 58092782, compound

Conditions

Temperature: 50 °C

Procedure

(3R,7aR)-7a-{[(3-Fluoro-benzyl)-methyl-amino]-methyl}-3-trichloromethyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one (Stage K.1, 385 mg, 0.973 mmol) was added to 7 M ammonia in MeOH (6.950 mL, 48.7 mmol) under argon and heated in a sealed vessel at 50° C. for 6 days and then at 75° C. for 5 days. The RM was then evaporated and the residue purified by flash chromatography using a 12 g RediSep® silica gel column (eluent 5% MeOH in DCM) to give the title compound as a yellow oil.

Workup

customThe RM was then evaporated
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-8193b50f6a3b45a99b2cb950647e0787
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357707B2

Reaction notes

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