Dicyclohexylcarbodiimide → Boc-ala-pro-OH

HRID 1589614Notes

Reaction equation

HRID 1589614 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].[NH:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 145742L-Proline

Product 1

HCID 11902919Boc-ala-pro-OH

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 25 ml of a solution of 0.68 g of Boc-Ala-OH in methylene chloride the H-Pro-resin described above was added and 5 ml of a solution of 0.74 g of DCC in methylene chloride was then added to the resulting mixture. The mixture was reacted at room temperature for 2 hours. After washing the resin 6 times with 30 ml of methylene chloride, the resin was added to 25 ml of a methylene chloride solution of 0.68 g of Boc-Ala-OH and 0.55 g of 1-hydroxybenzotriazole. Then, 5 ml of a methylene chloride solution of 0.74 g of DCC was added thereto and the resulting mixture was again reacted in a similar manner (double coupling). The resin was thoroughly washed with methylene chloride to obtain Boc-Ala-Pro-resin.

Workup

  1. additionabove was added
  2. customThe mixture was reacted at room temperature for 2 hours
  3. washAfter washing the resin 6 times with 30 ml of methylene chloride
  4. additionthe resin was added to 25 ml of a methylene chloride solution of 0.68 g of Boc-Ala-OH and 0.55 g of 1-hydroxybenzotriazole
  5. additionThen, 5 ml of a methylene chloride solution of 0.74 g of DCC was added
  6. customthe resulting mixture was again reacted in a similar manner (double coupling)
  7. washThe resin was thoroughly washed with methylene chloride

Sources & evidence

ORD record
ord-1a1d3a25f016400dbec6a682ec7ad63a
Source dataset
uspto-grants-1986_02
Patent number
US04572800

Reaction notes

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