Acetic Acid → BOC-Gly-Asn-Leu-Ser-Thr-OBzl

HRID 971583Notes

Reaction equation

HRID 971583 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:21]([NH:23][C@H:24]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C@@H:25]([CH3:27])[OH:26])=[O:22])[CH2:19][OH:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].FC(C(O)=O)(F)F.C(N(CC)CC)C.C(O)(=O)C.[CH3:56][C:57]([O:60][C:61]([NH:63][CH2:64][C:65](OC1C=CC([N+]([O-])=O)=CC=1)=[O:66])=[O:62])([CH3:59])[CH3:58]>CN(C)C=O.C(OCC)(=O)C>[NH:63]([C:61]([O:60][C:57]([CH3:59])([CH3:58])[CH3:56])=[O:62])[CH2:64][C:65]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:21]([NH:23][C@H:24]([C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[C@@H:25]([CH3:27])[OH:26])=[O:22])[CH2:19][OH:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:66]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 77217Boc-Gly-ONpHCID 131710006H-Asn-Leu-Ser-Thr-OBzl.TFA

Product 1

HCID 131710005BOC-Gly-Asn-Leu-Ser-Thr-OBzl

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

26.3 g of H-Asn-Leu-Ser-Thr-OBzl.TFA are dissolved in 100 ml of dimethylformamide, the solution is cooled to 0° C. and successively mixed with 7.5 ml of triethylamine, 0.54 ml of glacial acetic acid and a solution of 14.4 g of BOC-Gly-ONP in 100 ml of dimethylformamide, stirred at room temperature until the mixture solidifies and left to stand for 2 days. Thereafter 300 ml of ethyl acetate are added whilst stirring and the mixture left to stand overnight at -10° C. The precipitate is filtered off, washed twice with ethyl acetate and twice with ether, stirred for half an hour with 200 ml of water, filtered off, washed with water and dried in vacuo. Melting point 227°- 228° C.; [α]D = -23° (c = 2 in dimethylformamide); Rf9 = 0.50 (on silica gel).

Workup

  1. waitleft
  2. waitthe mixture left
  3. waitto stand overnight at -10° C
  4. filtrationThe precipitate is filtered off
  5. washwashed twice with ethyl acetate and twice with ether
  6. stirringstirred for half an hour with 200 ml of water
  7. filtrationfiltered off
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-80b34bd5114e45eebeab8cbdc9024f02
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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