L-Aspartic Acid → HCID 22807389, compound

HRID 1759291Notes

Reaction equation

HRID 1759291 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([NH:22][C@:23]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:28](O)=[O:29])[CH2:24][C:25]([OH:27])=[O:26])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C1CCC(N=C=NC2CCCCC2)CC1.N[C@H](C(O)=O)CC(O)=O>C(Cl)Cl.CCN(CC)CC>[C:15]([NH:22][C@:23]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:28]([NH:14][CH:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:29])[CH2:24][C:25](=[O:26])[OH:27])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

7

Reactant 4

HCID 5960L-Aspartic AcidHCID 7036BenzhydrylamineHCID 10868DicyclohexylcarbodiimideHCID 22807388HCID 22807388, compound

Product 1

HCID 22807389HCID 22807389, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Benzhydrylamine resin (10 g., 0.4 mmol/g.) was stirred with 250 ml. of 25% Et3N in CH2Cl2 for 10 minutes and then washed a few times with fresh CH2Cl2. It was then suspended in 240 ml. of CH2Cl2 and stirred with Boc-α-benzyl-L-aspartic acid (3.24 g., 10 mmol) and DCC (2.06 g., 10 mmol) for 17 hours. The amino acylated resin was collected, washed thoroughly with CH2Cl2, DMF and MeOH. It was dried and benzoylated with 1.5 ml. of pyridine and 1.65 ml. of benzoyl chloride in 110 ml. of CH2Cl2 for 15 minutes at 0° C. The resin was washed with CH2Cl2, MeOH to give 10.7 g. of desired material. Amino acid analysis indicated that there was 0.40 mmol/g. of aspartic acid.

Workup

  1. washwashed a few times with fresh CH2Cl2
  2. customThe amino acylated resin was collected
  3. washwashed thoroughly with CH2Cl2, DMF and MeOH
  4. customIt was dried
  5. washThe resin was washed with CH2Cl2, MeOH
  6. customto give 10.7 g

Sources & evidence

ORD record
ord-5755860150f64cb1aa52f5136f49f04c
Source dataset
uspto-grants-1982_07
Patent number
US04339427

Reaction notes

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