Hydrochloric Acid → HCID 86653241, compound

HRID 2169112Notes

Reaction equation

HRID 2169112 reaction equation
C([O:5][C:6](=[O:52])[C@@H:7]([NH:13][C:14](=[O:51])[CH2:15][CH2:16][C@@H:17]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[NH:18][C:19](=[O:43])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])(C)(C)C.[B-](F)(F)(F)F.CN(C(O[N:66]1[C:71](=[O:72])[CH2:70][CH2:69][C:67]1=[O:68])=[N+](C)C)C.CCN([CH:79]([CH3:81])[CH3:80])C(C)C.Cl.[C:83](#N)C>>[O:68]=[C:67]1[CH2:69][CH2:70][C:71](=[O:72])[N:66]1[O:5][C:6](=[O:52])[C@@H:7]([NH:13][C:14](=[O:51])[CH2:15][CH2:16][C@@H:17]([C:44]([O:46][C:47]([CH3:49])([CH3:48])[CH3:50])=[O:45])[NH:18][C:19](=[O:43])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:8][CH2:9][C:10]([O:12][C:79]([CH3:81])([CH3:83])[CH3:80])=[O:11]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6342Acetonitrile2×HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 58249242HCID 58249242, compound

Product 1

HCID 86653241HCID 86653241, compound

Procedure

(S)-2-[(S)-4-tert-Butoxycarbonyl-4-(17-tert-butoxycarbonylheptadecanoylamino)butyrylamino]-pentanedioic acid 1-tert-butyl ester (8 g, 10.79 mmol) was dissolved in acetonitrile (40 mL) and a solution of TSTU (3.89 g, 12.95 mmol) in acetonitrile (40 mL) was added. pH was adjusted to 8 by dropwise addition of DIPEA. The mixture was stirred at RT for 1 h, then acidified with HCl (2M) to pH 3 and evaporated in vacuo. This afforded an oil, which was subsequently partitioned between ethyl acetate and HCl (0.1 M). The organic layer was dried (MgSO4), filtered and evaporated to dryness in vacuo. This afforded 8.2 g of (S)-2-[(S)-4-tert-butoxycarbonyl-4-(17-tert-butoxycarbonylheptadecanoylamino)butyrylamino]pentanedioic acid 5-tert-butyl ester 1-(2,5-dioxopyrrolidin-1-yl)ester as a solid.

Workup

  1. customevaporated in vacuo
  2. customThis afforded an oil, which
  3. customwas subsequently partitioned between ethyl acetate and HCl (0.1 M)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d7ce2d61789341a39de3d51f0c0446c1
Source dataset
uspto-grants-2015_06
Patent number
US09045560B2

Reaction notes

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