Ethyl chloroformate → HCID 178473383, compound

HRID 576543Notes

Reaction equation

HRID 576543 reaction equation
[NH2:1]/[C:2](=[N:30]\[S:31]([C:34]1[C:35]([CH3:47])=[C:36]([CH3:46])[C:37]2[O:41][C:40]([CH3:43])([CH3:42])[CH2:39][C:38]=2[C:44]=1[CH3:45])(=[O:33])=[O:32])/[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([NH:16][S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)(=[O:19])=[O:18])[C:8](=[O:15])[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.Cl[C:58]([O:60][CH2:61][CH3:62])=[O:59]>C(Cl)(Cl)Cl>[CH2:61]([O:60][C:58]([N:12]1[CH2:11][CH2:10][N:9]([C:8](=[O:15])[C@@H:7]([NH:16][S:17]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)(=[O:19])=[O:18])[CH2:6][CH2:5][CH2:4][NH:3]/[C:2](/[NH2:1])=[N:30]/[S:31]([C:34]2[C:35]([CH3:47])=[C:36]([CH3:46])[C:37]3[O:41][C:40]([CH3:43])([CH3:42])[CH2:39][C:38]=3[C:44]=2[CH3:45])(=[O:33])=[O:32])[CH2:14][CH2:13]1)=[O:59])[CH3:62]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178427605HCID 178427605, compound

Product 1

HCID 178473383HCID 178473383, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of compound D (8.0 g, 11.1 mmol) in CHCl3 (50 ml) was added DIEA (4.1 mL, 23.3 mmol) at room temperature and stirred for 15 min. The mixture was cooled to ˜5° C., ethyl chloroformate (1.06 mL, 11.1 mmol) was added drop wise. After stirring at room temperature overnight (˜18 h), solvent removed in vacuo. The residue was dissolved in MeOH (˜25 ml) and Et2O (˜500 mL) was added. The precipitated crude product was filtered off, washed with Et2O and dried under vacuo to afford compound E (8.5 g, 11.1 mmol). LC-MS [M+H] 757.6 (C36H48N6O8S2+H, calc: 757.9). Compound E was used without further purification.

Workup

  1. stirringAfter stirring at room temperature overnight (˜18 h), solvent
  2. customremoved in vacuo
  3. dissolutionThe residue was dissolved in MeOH (˜25 ml)
  4. additionEt2O (˜500 mL) was added
  5. customThe precipitated crude product
  6. filtrationwas filtered off
  7. washwashed with Et2O
  8. customdried under vacuo

Sources & evidence

ORD record
ord-2d5a607eec14400c89f5b2278a6cd786
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

Loading…