Hydrochloric Acid → HCID 131717952, compound

HRID 1586696Notes

Reaction equation

HRID 1586696 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=O)[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[NH:40]1[CH2:58][CH2:57][CH2:56][C@H:41]1[C:42]([NH:44][C@H:45]([C:53]([NH2:55])=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:43]>C(OCC)(=O)C.CC(N(C)C)=O>[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([N:40]1[CH2:58][CH2:57][CH2:56][C@H:41]1[C:42]([NH:44][C@H:45]([C:53]([NH2:55])=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:43])=[O:16])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 1549350L-Phenylalaninamide, L-prolyl-HCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl ester

Product 1

HCID 131717952HCID 131717952, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

The mixed anhydride prepared by reacting Boc-Asp(OBzl) (5.82 g, 18 mmoles), N-methylmorpholine (1.98 mL, 18 mmoles) and isobutyl chloroformate (2.34 mL, 18 mmoles) in ethyl acetate (200 mL) at -15° C., was treated with the solution of HCl.Pro-Phe-NH2 (obtained above) and N-methylmorpholine (1.98 mL, 18 mmoles) in dimethylacetamide (40 mL). The reaction was allowed to proceed for 30 minutes at -15° C. and 2 hours at room temperature. The product was worked up as described earlier and reprecipitated from ethyl acetate-hexane.

Workup

  1. customat -15° C.
  2. customreprecipitated from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3569fbea563b4b74a9f16c43793d5436
Source dataset
uspto-grants-1993_06
Patent number
US05215964

Reaction notes

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