Diisopropylethylamine → HCID 117958509, compound

HRID 1482195Notes

Reaction equation

CCN(C(C)C)C(C)C.C(SC(=O)[CH2:19][CH2:20][C@H:21]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])C1C=CC=CC=1.Cl.[NH2:42][C@@H:43]([CH2:49][SH:50])[C:44]([O:46][CH2:47][CH3:48])=[O:45].C(CCP(CCC(O)=O)CCC(O)=O)(O)=[O:52]>CN(C=O)C.O>[C:36]([O:35][C:33]([NH:32][C@@H:21]([CH2:20][C:19]([NH:42][C@@H:43]([CH2:49][SH:50])[C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:52])[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])=[O:34])([CH3:37])([CH3:38])[CH3:39]

Participants

Conditions

Temperature: 50 °C

Procedure

DIPEA (0.098 ml, 0.563 mmol) was added to a solution of (S)-benzyl 5-(benzylthio)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoate (Compound 5b-2) (208.2 mg, 0.469 mmol) and (R)-ethyl 2-amino-3-mercaptopropanoate hydrochloride (104.5 mg, 0.563 mmol) in DMF (1.2 ml) and water (0.3 ml), and the mixture was stirred at 50° C. for three hours. A 0.4 M aqueous tris(2-carboxyethyl)phosphine (TCEP) solution (3.27 ml) and DMF (3.27 ml) were then added to the reaction solution, after which the mixture was stirred at room temperature for one hour. The reaction mixture was then purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→20/80) to afford (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-(((R)-1-ethoxy-3-mercapto-1-oxopropan-2-yl)amino)-4-oxobutanoate (Compound 5c-2) (192.4 mg, 88%).

Workup

stirringafter which the mixture was stirred at room temperature for one hour
customThe reaction mixture was then purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→20/80)

Sources & evidence

ORD record: ord-df0b5ee6662345cfb16f3843b1d09349
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409952B2

Reaction notes

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