Diisopropylethylamine → Glycyl-S-trityl-L-cysteinamide

HRID 630664Notes

Reaction equation

HRID 630664 reaction equation
C1C2C(COC([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:45]([NH2:47])=[O:46])[CH2:24][S:25][C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.CCN(C(C)C)C(C)C>CN(C)C=O>[NH2:18][CH2:19][C:20]([NH:22][C@H:23]([C:45]([NH2:47])=[O:46])[CH2:24][S:25][C:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:21]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 89544531N-[(9H-Fluoren-9-ylmethoxy)carbonyl]glycyl-S-trityl-L-cysteinamide

Product 1

HCID 89554940Glycyl-S-trityl-L-cysteinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.53 g (2.38 mmol) of the compound from example 17A was dissolved in 18 ml dimethyl formamide and 0.47 ml (4.79 mmol) DIEA was added. After one hour reaction time, the raw product was purified by preparative RP-HPLC on a C18 column with a water methanol gradient from 9/1 to 1/9. The product-containing fractions were combined and concentrated to dryness under reduced pressure. This gave 416 mg (0.97 mmol, 40% of theory) of the desired product.

Workup

  1. customAfter one hour reaction time
  2. customthe raw product was purified by preparative RP-HPLC on a C18 column with a water methanol gradient from 9/1 to 1/9
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-25d8f5a4762042d58572f81a2bff7a2d
Source dataset
uspto-grants-2016_04
Patent number
US09315543B2

Reaction notes

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