L-(+)-Cysteine → Boc-Cys(Dmb) Benzhydrylamine

HRID 622623Notes

Reaction equation

HRID 622623 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.[NH:15]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@H:16]([C:30]([OH:32])=[O:31])[CH2:17][S:18][CH2:19][C:20]1[CH:29]=[CH:28][C:25]([O:26][CH3:27])=[CH:24][C:21]=1[O:22][CH3:23].C1(N=C=NC2CCCCC2)CCCCC1.N[C@H](C(O)=O)CS.C1C=NC(C2C=C(Br)C=CC=2F)=C(F)C=1>C(Cl)Cl>[NH:15]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@H:16]([C:30]([OH:32])=[O:31])[CH2:17][S:18][CH2:19][C:20]1[CH:29]=[CH:28][C:25]([O:26][CH3:27])=[CH:24][C:21]=1[O:22][CH3:23].[CH:1]([NH2:14])([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

Participants

7

Reactant 5

HCID 5862L-(+)-CysteineHCID 7036BenzhydrylamineHCID 10868DicyclohexylcarbodiimideHCID 115435872-(5-Bromo-2-fluorophenyl)-3-fluoropyridineHCID 131715716Boc-Cys(Dmb)

Product 1

HCID 131715715Boc-Cys(Dmb) Benzhydrylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzhydrylamine-resin (BHA) (20 g, 0.5-0.7 meg/g) was coupled with Boc-Cys(Dmb)-OH (13.24g, 40.7mmol) in CH2Cl2 (250 mL) with dicyclohexyl carbodiimide (DCC) (8g,) for 4 hours. The resultant Boc-Cys(Dmb)-BHA- resin was washed with CH2Cl2 (3×300mL), DMF (2×300mL), MeOH (3×300mL), CH2Cl2 (3×300mL) and dried. An aliquot was hydrolyzed (1mL of 6M propionic HCl at 130° for 2 hours). Amino acid analysis showed a substitution of 0.52 mmol of Cys per gram of resin. The remaining amino groups were acetylated with AC2 0-pyridine - yield: 28.75g

Workup

  1. washThe resultant Boc-Cys(Dmb)-BHA- resin was washed with CH2Cl2 (3×300mL), DMF (2×300mL), MeOH (3×300mL), CH2Cl2 (3×300mL)
  2. customdried
  3. custom(1mL of 6M propionic HCl at 130° for 2 hours)

Sources & evidence

ORD record
ord-2710133351b5437092d6a1d6a217f890
Source dataset
uspto-grants-1988_09
Patent number
US04772547

Reaction notes

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