1,2-Dichloroethane → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2-((5-formylthiazol-2-yl)amino)acetamido)propanoate

HRID 1755485Notes

Reaction equation

HRID 1755485 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[N:5][CH:4]=1)=[O:2].Cl.[NH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([O:19][CH3:20])=[O:18].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>>[C:25]([O:24][C:22]([NH:21][C@@H:16]([CH2:15][NH:14][C:10](=[O:12])[CH2:9][NH:8][C:6]1[S:7][C:3]([CH:1]=[O:2])=[CH:4][N:5]=1)[C:17]([O:19][CH3:20])=[O:18])=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 181649HOAtHCID 11746086(S)-Methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoateHCID 867000852-((5-Formylthiazol-2-yl)amino)acetic acid

Product 1

HCID 86700128(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2-((5-formylthiazol-2-yl)amino)acetamido)propanoateYield 41.5%

Procedure

Following the general procedure as described in Example 24, except using 2-((5-formylthiazol-2-yl)amino)acetic acid, 1.00 HCl (150 mg, 0.674 mmol), (S)-methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate (see U.S. Publication No. 2007/93414 A1, 164 mg, 0.751 mmol), -1-hydroxy-7-azabenzotriazole (45 mg, 0.331 mmol), CH2C2 (5 mL), N-methylmorpholine (128 μL, 1.164 mmol), EDC (128 mg, 0.667 mmol) and stirring at room temp for 1 h, 108 mg (41.5%) of the title compound is isolated as an orange/red solid. Purification is done by BIOTAGE® Silica gel chromatography on a 20 g Thompson Single Step silica cartridge using a linear gradient from 100% CH2Cl2 to 100% EtOAc over 10 column volumes. LC/MS (Condition A): ret. T=2.54 min, (M+Na) 409.

Sources & evidence

ORD record
ord-e784784cfbb643f383d5d64e48c23183
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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