Phenyl chloroformate → HCID 68024116, compound

HRID 1406608Notes

Reaction equation

HRID 1406608 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C@:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([OH:19])[CH2:14][C:15]([CH3:18])([OH:17])[CH3:16])[CH3:9])=[CH:4][CH:3]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:11][CH2:12][C@@:13]([OH:19])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:14][C:15]([OH:17])([CH3:18])[CH3:16])[C:27](=[O:28])[O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15891Phenyl chloroformateHCID 68024046HCID 68024046, compound

Product 1

HCID 68024116HCID 68024116, compound

Conditions

Temperature
10 °C

Procedure

Preparation 2: Using a procedure similar to that described in Preparation 1 above, the reaction mixture from Step 4 above is cooled to about 10° C. and treated drop-wise with phenyl chloroformate (5.2 mL, 41.3 mmol). The reaction mixture is stirred at 20-25° C. for 2-18 hours, extracted with EtOAc, and the organic extract washed with 3N aqueous HCl. The combined organic phases are distilled to remove EtOAc and DME. The resultant solution is treated with heptane (30 mL), cooled to about 5° C., seeded with 5 (obtained from Preparation 1 immediately above), and held at about 5° C. for 3 hours. The resultant solids are collected by filtration, washed with heptane, and dried under vacuum at 25° C. for 18 hours to provide 5 as an off-white solid. Yield: 14.61 g, 78.3%; 97.2% purity by weight. Melting point: 129-131° C. LC-MS: 507.6/509.6 (95%, 100%); [M−H2O]+; calculated exact mass for M−H2O: 507.1.

Workup

  1. customPreparation 2
  2. extractionextracted with EtOAc
  3. extractionthe organic extract
  4. washwashed with 3N aqueous HCl
  5. distillationThe combined organic phases are distilled
  6. customto remove EtOAc and DME
  7. additionThe resultant solution is treated with heptane (30 mL)
  8. temperaturecooled to about 5° C.
  9. customobtained from Preparation 1 immediately above), and
  10. waitheld at about 5° C. for 3 hours
  11. filtrationThe resultant solids are collected by filtration
  12. washwashed with heptane
  13. customdried under vacuum at 25° C. for 18 hours

Sources & evidence

ORD record
ord-2f310f01b2cf44588612fed224de57d9
Source dataset
uspto-grants-2014_12
Patent number
US08916701B2

Reaction notes

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