Methanol → HCID 21356558, compound

HRID 1167452Notes

Reaction equation

HRID 1167452 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:14]2[CH2:18][CH2:17][C@@H:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)=[C:11]([F:13])[CH:12]=1)=[O:5])[CH3:2].C[C:28](C)([O-:30])C.C(OC(=O)CCC)[C@@H]1OC1.CO>O1CCCC1>[F:13][C:11]1[CH:12]=[C:7]([N:6]2[CH2:2][C@H:1]([CH2:28][OH:30])[O:3][C:4]2=[O:5])[CH:8]=[CH:9][C:10]=1[N:14]1[CH2:18][CH2:17][C@@H:16]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 45749132-Methylpropan-2-olateHCID 207256905-Ethoxycarbonylamino-2-((3R)-3-t-butoxycarbonylamino-1-pyrrolidinyl)fluorobenzene

Product 1

HCID 21356558HCID 21356558, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Ethoxycarbonylamino-2-((3R)-3-t-butoxycarbonylamino-1-pyrrolidinyl)fluorobenzene (33.6 g, 0.092 M) was dissolved in dry tetrahydrofuran (300 ml) under nitrogen. cooled to −70°, and treated dropwise over 30 minutes with a solution of lithiun t-butoxide (1 M in tetrahydrofuran, 100.7 ml), keeping the temperature below −65°. After stirring for 5 minutes, (R)-glycidylbutyrate (14.52 g, 0.101 M) was added, and stirring continued at −65° for 1 hour, before allowing the temperature to rise to ambient over 16 hours. The mixture was treated with MeOH (50 ml), stirred at ambient temperature for 1 hour, and the precipitate collected and washed well with tetrahydrofuran to give the desired product (21.8 g).

Workup

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

Sources & evidence

ORD record
ord-553006b2344442c8ac9fafa2f9a52d31
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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