Dimethylethylamine → HCID 86762227, compound

HRID 338122

Reaction equation

HRID 338122 reaction equation
[CH2:1]([N:4]1[CH2:12][CH:11]2[C:6]([C:22]3[S:23][CH:24]=[C:25]([Br:27])[CH:26]=3)([N:7]=[C:8]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:9][CH2:10]2)[CH2:5]1)[CH:2]=[CH2:3].CN(C)CC>C(O)C>[CH2:1]([N:4]1[CH2:12][C@@H:11]2[C@@:6]([C:22]3[S:23][CH:24]=[C:25]([Br:27])[CH:26]=3)([N:7]=[C:8]([NH:13][C:14](=[O:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:9][CH2:10]2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 11723DimethylethylamineHCID 89823511HCID 89823511, compound

Product 1

HCID 86762227HCID 86762227, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Racemic N-[6-Allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (2.24 g, 4.84 mmol) is purified by chiral HPLC: (Chiralpak AD 8×40.5 cm; eluent: 100% ethanol with 0.2% dimethylethyl amine); flow: 400 mL/min at UV 270 nm). Analysis conditions: Chiralpak AD-H 0.46×15 cm; eluent: 100% ethanol (0.2% isopropyl amine); flow: 0.6 mL/min at UV 320 nm; Rt=3.03 minutes. The second eluting isomer is isolated to give the title compound (1.08 g, 48%, >99% ee). ES/MS (m/e) (79Br/81Br) 462/464 (M+H).

Workup

  1. customThe second eluting isomer is isolated

Sources & evidence

ORD record
ord-48b90d5167094d57a2ef32fa6d77c3c7
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Linked notes

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