Acetic Acid → HCID 54562909, compound

HRID 1489791Notes

Reaction equation

HRID 1489791 reaction equation
[C:1]1([NH:7][C:8](=[O:45])[C@H:9]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH:10][C:11](=[O:40])[CH:12]([CH2:21][P:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]2=[O:39])([OH:24])=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:48])=[N-].C(O)(=O)C>ClCCl>[C:1]1([NH:7][C:8](=[O:45])[C@H:9]([CH2:41][CH:42]([CH3:43])[CH3:44])[NH:10][C:11](=[O:40])[CH:12]([CH2:21][P:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]2=[O:39])([O:24][CH3:48])=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 11764617HCID 11764617, compound

Product 1

HCID 54562909HCID 54562909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of dichloromethane (100 mL) and (2-(((4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl)hydroxyphosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamide (2.00 g, 3.17 mmol) from Example 1 was warmed to give a clear solution which was then cooled in an ice bath. Diazomethane (0.3M solution in ether) was added until the yellow color persisted and the solution was stired 10 min longer. Glacial acetic acid (0.080 mL, 84 mg, 1.4 mmol) was added to give a colorless solution which was concentrated under vacuum. Methanol (100 mL) was added and the solution was evaporated again and dried under vacuum to give 2.09 g of crude product which was used in the next reaction without further purification.

Workup

  1. temperaturewas warmed
  2. customto give a clear solution which
  3. temperaturewas then cooled in an ice bath
  4. customto give a colorless solution which
  5. concentrationwas concentrated under vacuum
  6. additionMethanol (100 mL) was added
  7. customthe solution was evaporated again
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b6fa14cc29544a0992f025ab21f7f184
Source dataset
uspto-grants-1997_10
Patent number
US05679700

Reaction notes

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