Tetrahydrofuran → HCID 86595550, compound

HRID 1477389Notes

Reaction equation

HRID 1477389 reaction equation
[CH2:1]1[C:3]2([CH2:8][CH:7]([C:9]([NH2:11])=[O:10])[CH2:6][NH:5][CH2:4]2)[CH2:2]1.[C:12](=[O:30])([O-])[O:13][CH:14]1[CH2:19][CH2:18][O:17][CH:16](C2C=CC([N+]([O-])=O)=CC=2)[CH2:15]1.[CH3:31][CH2:32][N:33]([CH:37]([CH3:39])C)[CH:34]([CH3:36])[CH3:35].[CH2:40]1[CH2:44][O:43][CH2:42][CH2:41]1>>[CH2:42]([O:43][NH:11][C:9]([C@H:7]1[CH2:8][C:3]2([CH2:2][CH2:1]2)[CH2:4][N:5]([C:12]([O:13][CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:30])[C@@H:6]1[C:9]([N:11]1[CH2:31][CH2:32][N:33]([C:34]2[CH:35]=[CH:8][CH:7]=[CH:6][CH:36]=2)[CH2:37][CH2:39]1)=[O:10])=[O:10])[C:41]1[CH:40]=[CH:44][CH:3]=[CH:1][CH:2]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 67007113HCID 67007113, compoundHCID 69287784HCID 69287784, compound

Product 1

HCID 86595550HCID 86595550, compound

Procedure

(6S,7S)—N-(benzyloxy)-6-((4-phenyl)piperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxamide (18.6 mg, 0.041 mmole) was mixed with 4-nitrophenyl-tetrahydropyran-4-yl carbonate (13.3 mg, 0.050 mmole), and DIEA (11.0 mg, 0.083 mmole) in THF and stirred at r.t. for 24 hours. After concentration, the crude material was purified with flash column to afford the desired product (6.0 mg) in quantitative yield.

Workup

  1. concentrationAfter concentration
  2. customthe crude material was purified with flash column

Sources & evidence

ORD record
ord-19d724b7c42041928cbca76f36739369
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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