Dicyclohexylcarbodiimide → HCID 178427592, compound

HRID 1066746Notes

Reaction equation

[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:2]([C:20]([OH:22])=O)[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].C1C=CC2N([OH:39])N=NC=2C=1.Cl.[CH2:41]([O:48][C:49](=[O:52])[CH2:50][NH2:51])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[CH3:53][CH2:54][N:55](C(C)C)C(C)C.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:1]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C@@H:2]([C:20]([NH:55][CH2:54][C:53]([NH:51][CH2:50][C:49]([O:48][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:52])=[O:39])=[O:22])[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]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of Boc-D-Arg(Tos)OH (11.2 g, 26.1 mmol), HOBt (3.9 g, 28.7 g), glycine benzyl ester hydrochloride (5.2 g, 26.1 mmol) in 52 mL of DCM is added DIEA (4.5 mL, 26.1 mmol) followed by DCC (5.9 g, 28.7 mmol; dissolved in 5 mL of DCM). After stirring for 18 h, the reaction mixture is cooled to −10° C. and the precipitate is filtered off. The filtrate is extracted twice with 1N Hcl (50 mL), twice with 5% NaHCO3 (50 mL), brine (50 mL), dried (MgSO4), and concentrated in vacuo to give 15.2 g (100%) of Boc-D-Arg(Tos)Gly-Gly-OBn as a white solid. RP-HPLC: 18.9 min.;C18, 0-100% CH3CN over 25 min., 1.5 mL/min.

Workup

filtrationthe precipitate is filtered off
extractionThe filtrate is extracted twice with 1N Hcl (50 mL), twice with 5% NaHCO3 (50 mL), brine (50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b020e6c808c1415fae00aa1ac629501f
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245743B1

Reaction notes

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