Hydrochloric Acid → HCID 58249280, compound

HRID 2361852Notes

Reaction equation

HRID 2361852 reaction equation
O=C1CCC(=O)N1[O:8][C:9](=[O:59])[C@@H:10]([NH:20][C:21](=[O:58])[CH2:22][CH2:23][C@@H:24]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[NH:25][C:26](=[O:50])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:11]CC(OC(C)(C)C)=O.[NH2:60][C@H:61]([C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])[CH2:62][CH2:63][C:64](=[O:66])[OH:65].Cl>C(#N)C.C([O-])([O-])=O.[Na+].[Na+]>[C:70]([O:69][C:67](=[O:68])[C@@H:61]([NH:60][C:9](=[O:8])[CH2:10][CH2:11][C@@H:10]([C:9]([O:8][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:59])[NH:20][C:21](=[O:58])[CH2:22][CH2:23][C@@H:24]([C:51]([O:53][C:54]([CH3:57])([CH3:55])[CH3:56])=[O:52])[NH:25][C:26](=[O:50])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:62][CH2:63][C:64]([OH:65])=[O:66])([CH3:73])([CH3:72])[CH3:71]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamateHCID 86653241HCID 86653241, compound

Product 1

HCID 58249280HCID 58249280, compoundYield 126.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

(S)-2-[(S)-4-tert-Butoxycarbonyl-4-(17-tert-butoxycarbonylheptadecanoylamino)butyrylamino]-pentanedioic acid 5-tert-butyl ester 1-(2,5-dioxopyrrolidin-1-yl) ester (4 g, 4.77 mmol) was dissolved in acetonitrile (30 mL) and added to a solution of H-Glu-OtBu (1.07 g, 5.25 mmol) in Na2CO3 (0.1 M, 20 mL). The mixture was stirred at RT for 1 h, then neutralised with HCl (2M) to pH 7 and evaporated in vacuo. The residual oil was subsequently partitioned between ethyl acetate and HCl (0.1 M). The organic layer was dried (MgSO4), filtered and evaporated to dryness in vacuo. The residue (4 g) was dissolved in acetonitrile and treated with active carbon. After filtration and evaporation to dryness followed by drying overnight in vacuo, 2.8 g of (S)-2-{(S)-4-tert-Butoxycarbonyl-4-[(S)-4-tert-butoxycarbonyl-4-(17-tert-butoxycarbonylheptadecanoylamino)butyrylamino]butyrylamino}pentanedioic acid 1-tert-butyl ester was obtained as a crystalline solid. LC-MS (electrospray): m/z=927 (M+1).

Workup

  1. customevaporated in vacuo
  2. customThe residual oil was subsequently partitioned between ethyl acetate and HCl (0.1 M)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. dissolutionThe residue (4 g) was dissolved in acetonitrile
  7. additiontreated with active carbon
  8. filtrationAfter filtration and evaporation to dryness
  9. customby drying overnight in vacuo

Sources & evidence

ORD record
ord-3b1ecf41bd264788ab881022502e1ed0
Source dataset
uspto-grants-2014_04
Patent number
US08691759B2

Reaction notes

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