(2R)-Oxiran-2-ylmethyl butanoate → HCID 21356569, compound

HRID 723749Notes

Reaction equation

HRID 723749 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:14]2[CH2:23][CH2:22][C:17]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:16][CH2:15]2)=[C:11]([F:13])[CH:12]=1)=[O:5])[CH3:2].C[C:25](C)([O-:27])C.[Li+].C(OC(=O)CCC)[C@@H]1OC1>O1CCCC1>[O:21]1[C:17]2([CH2:16][CH2:15][N:14]([C:10]3[CH:9]=[CH:8][C:7]([N:6]4[CH2:2][C@H:1]([CH2:25][OH:27])[O:3][C:4]4=[O:5])=[CH:12][C:11]=3[F:13])[CH2:23][CH2:22]2)[O:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 21876635HCID 21876635, compoundHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 21356569HCID 21356569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Ethoxycarbonylamino-2-(1,4-dioxa-8-azaspiro[4,5]dec-8-yl)fluorobenzene (22.9 g, 0.071 M) was dissolved in dry tetrahydrofuran (250 ml) under nitrogen, cooled to −70°, and treated dropwise over 30 minutes with a solution of lithium t-butoxide (1M in tetrahydrofuran, 77.6 ml), keeping the temperature below −70°. After stirring for 5 minutes, (R)-glycidylbutyrate (11.19 g, 0.077 M) was added, and stirring continued at −65° for 1 hour, before allowing the temperature to rise to ambient over 16 hours. The precipitate was collected and washed with tetrahydrofuran to give the desired product (17.8 g).

Workup

  1. temperaturecooled to −70°
  2. customthe temperature below −70°
  3. stirringstirring
  4. waitcontinued at −65° for 1 hour
  5. waitto ambient over 16 hours
  6. customThe precipitate was collected
  7. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-a4ef36268ced4a26a5a902f91a01a681
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

Loading…