Phenylmethanesulfonyl chloride → HCID 178427609, compound

HRID 1066747Notes

Reaction equation

HRID 1066747 reaction equation
[NH2:1][C@@H:2]([C:20]([NH:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[CH2:34]([S:41](Cl)(=[O:43])=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH2:34]([S:41]([NH:1][C@@H:2]([C:20]([NH:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=1)(=[O:11])=[O:10])(=[O:43])=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 178427563D-Arg(Tos)-Gly-OBn

Product 1

HCID 178427609HCID 178427609, compoundYield 97%

Conditions

Temperature
23 °C

Procedure

To a solution of D-Arg(Tos)-Gly-OBn (5.2 mmol; Boc previously removed by treatment with 40% TFA/DCM (0.1M) for 15 min. and then concentrated in vacuo; RP-HPLC: 13.8 min.; C18, 0-100% CH3CN over 25 min., 1.5 mL/min) in 21 mL of DCM is neutralized with DIEA before cooling to −78° C. where 1.19 g (6.24 mmol) of BnSO2Cl is added as a solid followed by 900 uL (10.4 mmol). The solution is allowed to warm to 23° C. and stirr for 18 h. The eaction mixture was extracted twice with 10% citric acid, twice with 5% NaHCO3 (50 mL), brine (50 mL), dried (MgSO4), and concentrated in vacuo to give 3.2 g (97%) of BnSO2-D-Arg(Tos)Gly-OBn as a white solid. RP-HPLC: 18.0 min.;C18, 0-100% CH3CN over 25 min., 1.5 mL/min.

Workup

  1. customBoc previously removed by treatment with 40% TFA/DCM (0.1M) for 15 min.
  2. concentrationconcentrated in vacuo
  3. custom13.8 min.
  4. additionis added as a solid
  5. waitstirr for 18 h
  6. extractionThe eaction mixture was extracted twice with 10% citric acid, twice with 5% NaHCO3 (50 mL), brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-314b12be7f3e4948b21082d75c4e4a2b
Source dataset
uspto-grants-2001_06
Patent number
US06245743B1

Reaction notes

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