Nitrite → HCID 131714607, compound

HRID 246922Notes

Reaction equation

[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:25]([NH:27][C@H:28]([C:33]([NH:35][C@H:36]([C:39]([NH:41][NH2:42])=[O:40])[CH2:37][OH:38])=[O:34])[CH2:29][C:30](=[O:32])[NH2:31])=[O:26])[C@@H:22]([CH3:24])[OH:23])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].Cl.O1CCOCC1.[N:57]([O-])=O.C(N(C(C)C)CC)(C)C>CS(C)=O.CN(C=O)C>[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:25]([NH:27][C@H:28]([C:33]([NH:35][C@H:36]([C:39]([N:41]=[N+:42]=[N-:57])=[O:40])[CH2:37][OH:38])=[O:34])[CH2:29][C:30](=[O:32])[NH2:31])=[O:26])[C@@H:22]([CH3:24])[OH:23])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

Conditions

Temperature: -25 °C

Procedure

5.94 g (8.55 mM) of Boc-Ile-Phe-Thr-Asn-Ser-NH-NH2 are dissolved in 27 ml of DMSO plus 37 ml of DMF. After cooling to -25° C., 6.1 ml of a 5.6 N HCl/dioxane solution then 1.23 ml of tertiobutyl nitrite (1.2 equiv.) prediluted in 5 ml of DMF precooled to -20° C., are added. After 1 hr. 15 mins. of stirring between -20° and -25° C., 6.1 ml of diisopropylethylamine (DIPEA) are added to take the pH to around 6, then 3 ml of DMF are added to take the volume to 85 ml and this solution is conserved at -25° C.

Workup

customprecooled to -20° C.
additionare added
custom15 mins
customis conserved at -25° C.

Sources & evidence

ORD record: ord-208c44d84087413db4bfab94a1f4f8c0
Source dataset: uspto-grants-1987_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04704450

Reaction notes

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