Diisopropylethylamine → 6-Amino-N-[(2R)-1-amino-1-oxo-3-(tritylsulfanyl)propan-2-yl]hexanamide

HRID 630666Notes

Reaction equation

HRID 630666 reaction equation
C1C2C(COC(=O)[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][C@@H:26]([CH2:30][S:31][C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([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]([NH2:29])=[O:28])=[O:24])C3C(=CC=CC=3)C=2C=CC=1.CCN(C(C)C)C(C)C>CN(C)C=O>[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][C@@H:26]([CH2:30][S:31][C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:27]([NH2:29])=[O:28])=[O:24]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 895550309H-Fluoren-9-ylmethyl-(6-{[(2R)-1-amino-1-oxo-3-(tritylsulfanyl)propan-2-yl]amino}-6-oxohexyl)carbamate

Product 1

HCID 895450906-Amino-N-[(2R)-1-amino-1-oxo-3-(tritylsulfanyl)propan-2-yl]hexanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

678 mg (0.97 mmol) of the compound of example 20A was dissolved in 7 ml dimethyl formamide and 0.19 ml (1.94 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 457 mg (0.93 mmol, 95% 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-c69c5f60fc3e4d40acb157cabbe5243a
Source dataset
uspto-grants-2016_04
Patent number
US09315543B2

Reaction notes

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